Pyridine → (3-Propyloxetan-3-yl)methyl hex-5-ynoate

HRID 1197311Notes

Reaction equation

HRID 1197311 reaction equation
[OH:1][CH2:2][C:3]1([CH2:7][CH2:8][CH3:9])[CH2:6][O:5][CH2:4]1.N1C=[CH:14][CH:13]=[CH:12][CH:11]=1.CC[O:18][CH2:19][CH3:20]>>[C:19]([O:1][CH2:2][C:3]1([CH2:7][CH2:8][CH3:9])[CH2:6][O:5][CH2:4]1)(=[O:18])[CH2:20][CH2:14][CH2:13][C:12]#[CH:11]

Participants

4

Reactant 3

HCID 1049PyridineHCID 3283Diethyl Ether2×HCID 1838902-Propyl-2-oxetanemethanol

Product 1

HCID 19373318(3-Propyloxetan-3-yl)methyl hex-5-ynoate

Procedure

A mixture of hex-5-ynoic acid (1 g) and thionyl chloride (1.95 ml) in benzene (25 ml) was heated under reflux for 3 hours. The resulting solution was cooled and then evaporated in vacuo. The acid halide thus obtained was taken up in ether (5 ml) and added, dropwise, to a stirred solution of 3-hydroxymethyl-3-n-propyloxetane (1.2 g) and pyridine (0.8 ml) in dry ether (20 ml.). The reaction mixture was stirred at room temperature for 16 hours. After this time the organic phase was washed with water, 5% hydrochloric acid, saturated sodium bicarbonate solution and brine before drying over anhydrous magnesium sulphate and then evaporation in vacuo. The residue was purified by chromatography on silica, pre-eluted with hexane containing 1% triethylamine. Elution with hexane/ether mixtures gave (3-propyloxetan-3-yl)methyl hex-5-ynoate (1.33 g) as a colourless oil.

Workup

  1. additionadded
  2. washAfter this time the organic phase was washed with water, 5% hydrochloric acid, saturated sodium bicarbonate solution and brine
  3. dry with materialbefore drying over anhydrous magnesium sulphate
  4. customevaporation in vacuo
  5. customThe residue was purified by chromatography on silica
  6. washpre-eluted with hexane containing 1% triethylamine
  7. washElution with hexane/ether mixtures

Sources & evidence

ORD record
ord-8dbfc778e7634e7d8976d2562d223954
Source dataset
uspto-grants-1992_05
Patent number
US05116862

Reaction notes

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