(R)-(-)-3-Hydroxytetrahydrofuran Chemical Properties

alpha 

-18.5 º (c=2 MeOH)

Boiling point:

181 °C (lit.)

Density 

1.097 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.45(lit.)

Flash point:

180 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform, Methanol (Slightly)

form 

Liquid

pka

14.49±0.20(Predicted)

color 

Clear colorless

Specific Gravity

1.097

optical activity

[α]20/D 18°, c = 2.4 in methanol

InChI

InChI=1S/C4H8O2/c5-4-1-2-6-3-4/h4-5H,1-3H2/t4-/m1/s1

InChIKey

XDPCNPCKDGQBAN-SCSAIBSYSA-N

SMILES

O1CC[C@@H](O)C1

CAS DataBase Reference

86087-24-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

NA 1993 / PGIII

WGK Germany 

3

HazardClass 

CBL

HS Code 

29321900

MSDS

• Language:English Provider:SigmaAldrich

(R)-(-)-3-Hydroxytetrahydrofuran Usage And Synthesis

Chemical Properties

Colorless to light yellow liqui

Uses

(R)-(-)-3-Hydroxytetrahydrofuran is used as a chemical reactant in the synthesis of pharmaceutical agents. Empagliflozin is synthesized using this reactant

Uses

(R)-(-)-3-Hydroxytetrahydrofuran may be used as building block in the synthesis of potent HIV protease inhibitors.

Synthesis

Example 5 Preparation of (R)-3-hydroxytetrahydrofuran: 35 g (0.28 mol) of (R)-4-chloro-1,3-butanediol made in reference to Example 2 was dissolved in 70 mL of 0.5 N hydrochloric acid solution and the reaction was heated under reflux conditions for 2 hours. Upon completion of the reaction, it was cooled to room temperature and the reaction mixture was neutralized with 50% aqueous sodium hydroxide solution, followed by evaporation under reduced pressure to remove water. To the residual crystals and oily mixture, 60 mL of methanol was added and mixed with thorough stirring. Insoluble crystals were removed by filtration and the filtrate was concentrated under reduced pressure. Finally, the concentrated residue was distilled under reduced pressure to give 16.6 g of (R)-(-)-3-hydroxytetrahydrofuran in the form of colorless liquid (purity: 99.1%; yield: 67%). Its rotundity was determined as [α]D23 = -15.91° (c = 2.45, methanol).

References

[1] Patent: US5780649, 1998, A
[2] Patent: WO2008/93955, 2008, A1. Location in patent: Paragraph 65-66
[3] Patent: WO2016/21192, 2016, A1. Location in patent: Paragraph 0085

(R)-(-)-3-Hydroxytetrahydrofuran(86087-24-3)Related Product Information

• 2-Methyltetrahydrofuran
• Tetrahydrofuran
• 2,3,4,6-TETRA-O-PIVALOYL-ALPHA-D-GLUCOPYRANOSYL BROMIDE
• Acetoxy Empagliflozin
• (2-Chloro-5-iodophenyl)(4-fluorophenyl)methanone
• (R)-3-(4-(5-broMo-2-chlorobenzyl)phenoxy)tetrahydrofuran
• (3R,4S,5S,6R)-2-[4-chloro-3-[[4-[(3S)-oxolan-3-yl]oxyphenyl]methyl]phenyl]-6-(hydroxymethyl)-2-methoxyoxane-3,4,5-triol
• EMpagliflozin iMpurity 10
• Butanoic acid, 4-chloro-3-hydroxy-, (3S)-
• Methanone, (5-chloro-2-iodophenyl)(2-fluorophenyl)-
• (5-bromo-2-chlorophenyl)(4-fluorophenyl)methanone
• 1-chloro-4-(β-D-glucopyranos-1-yl)-2-[4-((S)-tetrahydrofuran-3-yloxy)benzyl]benzene
• Empagliflozin Impurity 32
• 4-(pyridine-2-yl) pyrimidin-2-amine
• (2-Chloro-5-iodophenyl)[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl]methanone
• (S)-(5-broMo-2-chlorophenyl)(4-(tetrahydrofuran-3-yloxy)phenyl)Methanone
• EMpagliflozin iMpurity 13
• Empagliflozin Impurity