(S)-(+)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID Chemical Properties

Melting point:

71-73 °C (lit.)

alpha 

+14°(20/D, c=5, CH3OH)

Boiling point:

150-155 °C/0.2 mmHg (lit.)

Density 

1.3985 (rough estimate)

refractive index 

1.5800 (estimate)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Acetone

form 

Solid

pka

3.11±0.20(Predicted)

color 

White

optical activity

[α]20/D +14°, c = 5 in methanol

BRN 

1424498

InChI

InChI=1S/C5H6O4/c6-4-2-1-3(9-4)5(7)8/h3H,1-2H2,(H,7,8)/t3-/m0/s1

InChIKey

QVADRSWDTZDDGR-VKHMYHEASA-N

SMILES

O1C(=O)CC[C@H]1C(O)=O

CAS DataBase Reference

21461-84-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29321900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

(S)-(+)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID Usage And Synthesis

Chemical Properties

white to light yellow to beige crystalline powder

Uses

(S)-5-Oxo-2-tetrahydrofurancarboxylic Acid (cas# 21461-84-7) is a compound useful in organic synthesis.

Definition

ChEBI: (S)-alpha-hydroxyglutaric acid-gamma-lactone is a butan-4-olide obtained by formal intramolecular condensation between the 2-hydroxy and 4-carboxy groups of (S)-2-hydroxyglutaric acid It is a butan-4-olide and a monocarboxylic acid. It is functionally related to a (S)-2-hydroxyglutaric acid. It is a conjugate acid of a (S)-alpha-hydroxyglutarate-gamma-lactone.

General Description

(S)-(+)-5-Oxo-2-tetrahydrofurancarboxylic acid is a chiral derivatizing agent for alcohols.

Synthesis

General procedure for the synthesis of (S)-5-oxo-2-tetrahydrofuran carboxylic acid from L-glutamic acid: L-glutamic acid (10.07 g, 0.068 mol, JK CHEMICA) was dissolved in 20 mL of water in a conical flask. A solution of NaNO2 (7.0 g, 0.102 mol, Shantou Xilong Chemical Factory) in 20 mL of water was slowly added to this solution at -5°C, along with HCl and 40 mL of water. The reaction mixture was stirred continuously at room temperature for 12 hours. Subsequently, the reaction mixture was subjected to vacuum evaporation at less than 50 °C to obtain a yellow oily substance. This oily substance was dissolved in EtOAc, filtered to remove the solid formed and the solid was washed with EtOAc. The filtrate and washings were combined and dried with Na2SO4. Finally, the solvent was removed by vacuum concentration to afford (S)-5-oxo-2-tetrahydrofuran carboxylic acid as a light yellow oil (8.1 g, 91.6% yield). The product was analyzed by mass spectrometry (ESI, cation mode), m/z: 130.9 (M+1); 1H NMR (400 MHz, CDCl3) data were as follows: δ 2.27-2.41 (m, 1H), 2.44-2.65 (m, 3H), 5.09 (m, 1H), 9.12-9.55 (m, 1H).

References

[1] Journal of Organic Chemistry, 2010, vol. 75, # 2, p. 390 - 398
[2] Patent: WO2010/45095, 2010, A1. Location in patent: Page/Page column 69; 70
[3] Synthesis, 2007, # 15, p. 2279 - 2286
[4] Tetrahedron, 2009, vol. 65, # 48, p. 9997 - 10001
[5] Carbohydrate Research, 1983, vol. 124, p. 35 - 42

(S)-(+)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID(21461-84-7)Related Product Information

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• (S)-(+)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID
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• (R)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID,(R)-(-)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID
• 2,2-DIMETHYL-5-OXOTETRAHYDROFURAN-3-CARBOXYLIC ACID
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• (S)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID,(S)-(+)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID,5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID
• (R)-(-)-DIHYDRO-5-(HYDROXYMETHYL)-2(3H)-FURANONE
• HYDROXYCITRIC ACID LACTONE, (-)-(P)
• 2-(1-Carboxyundecyl)-5-oxotetrahydrofuran-2-carboxylic acid
• (3S)-2-(2-METHOXYPHENYL)-5-OXOTETRAHYDROFURAN-3-CARBOXYLIC ACID
• 4-METHYLENE-2-OCTYL-5-OXOTETRAHYDROFURAN-3-CARBOXYLIC ACID
• 2-[[(4S)-4-[[(2,6-Difluorophenyl)acetyl]amino]-3-oxotetrahydroisoxazol]-2-yl]-5-oxotetrahydrofuran-2-carboxylic acid sodium salt
• 3-Methyl-4-methylene-2-oxotetrahydrofuran-3-carboxylic acid ethyl ester
• 4-Isopropenyl-3-methyl-2-oxotetrahydrofuran-3-carboxylic acid ethyl ester
• 2-[[(4S)-4-[[(2-Amino-4-thiazolyl)acetyl]amino]-3-oxotetrahydroisoxazol]-2-yl]-5-oxotetrahydrofuran-2-carboxylic acid sodium salt
• 2-[[(4S)-4-[[(4-Pyridinylthio)acetyl]amino]-3-oxotetrahydroisoxazol]-2-yl]-5-oxotetrahydrofuran-2-carboxylic acid sodium salt