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

HRID 401861Notes

Reaction equation

HRID 401861 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16](=[O:21])[CH2:17][CH2:18][CH2:19][CH3:20])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22]([O:24][C:25](=[O:28])[CH:26]=[O:27])[CH3:23]>C1(C)C=CC=CC=1.C(N(CC)CC)C.C(Cl)Cl>[CH2:22]([O:24][C:25](=[O:28])[CH:26]([OH:27])[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:21])[CH2:17][CH2:18][CH2:19][CH3:20])[CH3:23]

Participants

6

Reactant 2

HCID 70211Ethyl oxoacetateHCID 673734141-(4-Benzyloxy-phenyl)-hexan-2-one

Product 1

HCID 673735133-(4-Benzyloxy-phenyl)-2-hydroxy-4-oxo-octanoic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 1-(4-benzyloxy-phenyl)-hexan-2-one (40.36 mmol, 11.4 g), oxo-acetic acid ethyl ester solution in toluene (30 mL, 50% solution in toluene) and triethylamine (15 mL) was stirred at ambient temperature for 16 h. The reaction mixture was diluted with DCM (300 mL), washed with water (3×100 mL), and the organic layer was dried and concentrated under reduced pressure. The resultant residue was purified by flash silica gel chromatography eluting with 30% ethyl acetate in hexanes to provide 3-(4-benzyloxy-phenyl)-2-hydroxy-4-oxo-octanoic acid ethyl ester.

Workup

  1. washwashed with water (3×100 mL)
  2. customthe organic layer was dried
  3. concentrationconcentrated under reduced pressure
  4. customThe resultant residue was purified by flash silica gel chromatography
  5. washeluting with 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-011feab4c39a48238ea7ce2ac1534ded
Source dataset
uspto-grants-2014_06
Patent number
US08741900B2

Reaction notes

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