Sodium hydride → Ethyl 2-[4-(1-ethoxycarbonyl-2-oxocyclohexan-1-ylmethyl)phenyl]propionate

HRID 971875Notes

Reaction equation

[H-].[Na+].[CH3:3][CH2:4][O:5][C:6]([CH:8]1[C:13](=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7].Cl[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]([CH3:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:19][CH:18]=1>CN(C)C=O>[CH2:4]([O:5][C:6]([C:8]1([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([CH:23]([CH3:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:21][CH:22]=2)[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1=[O:14])=[O:7])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of 9.6 g of 50% sodium hydride and 200 ml of dimethyl formamide was added dropwise 34 g of ethyl 2-cyclohexanone carboxylate under ice-cooling, the mixture was stirred at 50° C. for 30 minutes, thereafter again under ice-cooling 45.3 g of ethyl 2-(p-chloromethylphenyl)propionate was added dropwise, and the mixture was heated at 50°-60° C. with stirring for 1 hour. After the reaction was completed, the reaction mixture was poured into an ice-water, extracted with ether, the extract washed with water, dried over anhydrous sodium sulfate, and the solvent removed by distillation to give 69.5 g of an oily substance, which was subjected to a vacuum distillation affording 57 g of the dsired compound as a colorless oily substance, b.p. 200°-205° C. at 0.4 mm Hg.

Workup

temperaturecooling
additionwas added dropwise
temperaturethe mixture was heated at 50°-60° C.
stirringwith stirring for 1 hour
extractionextracted with ether
washthe extract washed with water
dry with materialdried over anhydrous sodium sulfate
customthe solvent removed by distillation
customto give 69.5 g of an oily substance, which
distillationwas subjected to a vacuum distillation

Sources & evidence

ORD record: ord-a74569ad2e01443da9db5b2dcd14cc73
Source dataset: uspto-grants-1979_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04161538

Reaction notes

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