Pyridine → HCID 19373318, compound

HRID 129262Notes

Reaction equation

HRID 129262 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 19373318HCID 19373318, compound

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-e859a26335c942b19b5c3d18e93a0a39
Source dataset
uspto-grants-1995_11
Patent number
US05466710

Reaction notes

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