TETRAHYDRO-2-(2-PROPYNYLOXY)-2H-PYRAN Chemical Properties

Boiling point:

63-65 °C9 mm Hg(lit.)

Density 

0.997 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.458(lit.)

Flash point:

139 °F

storage temp. 

2-8°C

form 

Liquid

color 

Clear colorless to light yellow

Specific Gravity

0.997

InChI

InChI=1S/C8H12O2/c1-2-6-9-8-5-3-4-7-10-8/h1,8H,3-7H2

InChIKey

RNRIMDSCBRDPLC-UHFFFAOYSA-N

SMILES

C1(OCC#C)OCCCC1

CAS DataBase Reference

6089-04-9

Safety Information

Hazard Codes 

Xi,F

Risk Statements 

11

Safety Statements 

26-27-28-36/37/39-16

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

HazardClass 

3.2

PackingGroup 

III

HS Code 

29329900

MSDS

• Language:English Provider:SigmaAldrich

TETRAHYDRO-2-(2-PROPYNYLOXY)-2H-PYRAN Usage And Synthesis

Chemical Properties

Clear colorless to light yellow liquid

Uses

Tetrahydro-2-(2-propynyloxy)-2H-pyran was used in preparation of 1,3-dienyl acetal.

Synthesis Reference(s)

Chemistry Letters, 6, p. 817, 1977
Organic Syntheses, Coll. Vol. 7, p. 334, 1990
Synthetic Communications, 19, p. 901, 1989 DOI: 10.1080/00397918908051010

General Description

The anion formed by metalation at the acetylenic carbon reacts with a variety of electrophiles.

Synthesis

General procedure for the synthesis of O-THP propargyl alcohol (Compound 18) from 3,4-dihydro-2H-pyran and 2-propyn-1-ol: Compound 18 was prepared according to literature procedure. To a solution of propargyl alcohol 17 (2.6 mL, 44.6 mmol) and p-toluenesulfonic acid monohydrate (0.09 g, 0.5 mmol) in dichloromethane (45 mL) was added dropwise 3,4-dihydro-2H-pyran (4.3 mL, 46.8 mmol) at 0 °C. The reaction mixture was stirred at 0 °C for 5 min before slowly warming up to room temperature and continued stirring for 1 h. The reaction mixture was then purified with aqueous solution of saturated 2H-pyran (4.3 mL). Subsequently, the reaction mixture was washed with saturated sodium bicarbonate solution (30 mL) and the aqueous layer was extracted with dichloromethane (45 mL). The organic layers were combined, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give compound 18 (6.1 g, 97.2% yield) as a yellow oil. Thin layer chromatography (TLC) Rf = 0.30 (hexane/ether, 95:5). 1H NMR (400 MHz, CDCl3): δ = 1.50-1.67 (m, 4H), 1.70-1.89 (m, 2H), 2.41 (t, J = 2.4 Hz, 1H), 3.52-3.57 (m, 1H), 3.82-3.87 (m , 1H), 4.27 (ddd, J = 2.4 Hz, 11.3 Hz, 15.8 Hz, 2H), 4.83 (t, J = 3.4 Hz, 1H). 13C NMR (100 MHz, CDCl3): δ = 19.0, 25.3, 30.2, 53.9, 61.9, 74.0, 79.7, 96.8. mass spectra (MS-CI): m/z calculated values. ): m/z calculated value C8H12O2 [M + H]+, 141; measured value: 141. The synthesis of this compound has been reported in the literature.

References

[1] Synlett, 2003, # 14, p. 2163 - 2166
[2] Tetrahedron, 2010, vol. 66, # 25, p. 4573 - 4576
[3] Synthesis, 2005, # 19, p. 3293 - 3296
[4] Journal of the Chinese Chemical Society, 2007, vol. 54, # 2, p. 525 - 532
[5] Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1531 - 1540

TETRAHYDRO-2-(2-PROPYNYLOXY)-2H-PYRAN(6089-04-9)Related Product Information

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