Triethylamine → 4-Cyclohexyl-3-(4-cyclohexyloxy-phenyl)-2-hydroxy-4-oxo-butyric acid ethyl ester

HRID 1971987Notes

Reaction equation

HRID 1971987 reaction equation
[CH:1]1([C:7](=[O:22])[CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:30]([O:34][CH2:35][CH3:36])(=[O:33])[CH:31]=[O:32]>C1COCC1>[CH2:35]([O:34][C:30](=[O:33])[CH:31]([OH:32])[CH:8]([C:9]1[CH:10]=[CH:11][C:12]([O:15][CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)=[CH:13][CH:14]=1)[C:7]([CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)=[O:22])[CH3:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70211Ethyl oxoacetateHCID 673746771-Cyclohexyl-2-(4-cyclohexyloxy-phenyl)-ethanone

Product 1

HCID 673757224-Cyclohexyl-3-(4-cyclohexyloxy-phenyl)-2-hydroxy-4-oxo-butyric acid ethyl esterYield 59.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-cyclohexyl-2-(4-cyclohexyloxy-phenyl)-ethanone (1.17 mmol, 0.35 g) and triethylamine (1.17 mmol, 0.16 mL) in THF (1.0 mL) was added a solution of ethyl glyoxylate (50% in toluene, 5.83 mmol, 1.15 mL) and continued stirring for 12 h at room temperature. After removal of volatiles under reduced pressure, the crude product was purified on a 24 g SiO2 cartridge using an ethyl acetate/hexanes gradient to give 4-cyclohexyl-3-(4-cyclohexyloxy-phenyl)-2-hydroxy-4-oxo-butyric acid ethyl ester (0.28 g).

Workup

  1. customAfter removal of volatiles under reduced pressure
  2. customthe crude product was purified on a 24 g SiO2 cartridge

Sources & evidence

ORD record
ord-582476c338b144b89c694f2864c46024
Source dataset
uspto-grants-2013_04
Patent number
US08431575B2

Reaction notes

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