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

HRID 2168615Notes

Reaction equation

HRID 2168615 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-2800212b6ece446b865453b230fe1849
Source dataset
uspto-grants-2015_06
Patent number
US09045461B2

Reaction notes

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