Hydrochloric Acid → 2-(8-Hydroxy-7-oxo-octyl)cyclopent-2-en-1-one

HRID 127090Notes

Reaction equation

Cl[C:2]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[C:11](=[O:15])[CH2:12][CH2:13][CH:14]=1)=[O:3].[O:16]1CCOC[CH2:17]1.Cl>[Cl-].[Na+].O>[OH:16][CH2:17][C:2](=[O:3])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[C:11](=[O:15])[CH2:12][CH2:13][CH:14]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 6.3 g of 2-[6-(chloroformyl)hexyl]cyclopent-2-en-1-one (Example 268) and 16 g of tris-trimethylsilyloxyethylene (Example 267) are stirred at 90° to 100° C. under argon for one hour. To this mixture is added 25 ml of dioxane and 10 ml of 0.6 N hydrochloric acid. The mixture is heated at 80° C. for 30 minutes. The mixture is poured into brine and extracted with ether. The ether solution is washed with saturated sodium bicarbonate and dried over magnesium sulfate. The solvent is removed and the residue is chromatographed on a dry column of silica gel eluting with ether containing 2% acetic acid to give 1.7 g of the title compound (Rf =0.45).

Workup

extractionextracted with ether
washThe ether solution is washed with saturated sodium bicarbonate
dry with materialdried over magnesium sulfate
customThe solvent is removed
customthe residue is chromatographed on a dry column of silica gel eluting with ether containing 2% acetic acid

Sources & evidence

ORD record: ord-4b89c014b8504f3f93f91321c067ddf6
Source dataset: uspto-grants-1981_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04254285

Reaction notes

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