Ethyl oxoacetate → 3-(4-Benzyloxy-phenyl)-2-hydroxy-4-oxo-heptanoic acid ethyl ester

HRID 401887Notes

Reaction equation

HRID 401887 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16](=[O:20])[CH2:17][CH2:18][CH3:19])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]([O:23][C:24](=[O:27])[CH:25]=[O:26])[CH3:22]>C1(C)C=CC=CC=1.C(N(CC)CC)C>[CH2:21]([O:23][C:24](=[O:27])[CH:25]([OH:26])[CH:15]([C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:14][CH:13]=1)[C:16](=[O:20])[CH2:17][CH2:18][CH3:19])[CH3:22]

Participants

5

Reactant 2

HCID 70211Ethyl oxoacetateHCID 673733611-(4-Benzyloxy-phenyl)-pentan-2-one

Product 1

HCID 673740033-(4-Benzyloxy-phenyl)-2-hydroxy-4-oxo-heptanoic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 1-(4-benzyloxy-phenyl)-pentan-2-one (2.98 mmol, 11.4 g), oxo-acetic acid ethyl ester solution in toluene (8 mL, 50% solution in toluene) and triethylamine (2 mL) was stirred at ambient temperature for 24 h. The volatiles were removed under reduced pressure, and the resultant residue was purified by flash silica gel chromatography using by eluting with 30% ethyl acetate in hexanes to provide 3-(4-benzyloxy-phenyl)-2-hydroxy-4-oxo-heptanoic acid ethyl ester.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe resultant residue was purified by flash silica gel chromatography
  3. washby eluting with 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-01aaf177b4544f90898b7f97d17205e5
Source dataset
uspto-grants-2014_06
Patent number
US08741900B2

Reaction notes

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