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

HRID 402003Notes

Reaction equation

HRID 402003 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:15][C:16](=[O:21])[CH2:17][CH2:18][CH2:19][CH3:20])[CH:5]=[CH:6][C:7]=1[O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]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:4]1[CH:5]=[CH:6][C:7]([O:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[C:2]([Br:1])[CH:3]=1)[C:16](=[O:21])[CH2:17][CH2:18][CH2:19][CH3:20])[CH3:23]

Participants

6

Reactant 2

HCID 70211Ethyl oxoacetateHCID 673736281-(3-Bromo-4-cyclohexyloxy-phenyl)-hexan-2-one

Product 1

HCID 673752833-(3-Bromo-4-cyclohexyloxy-phenyl)-2-hydroxy-4-oxo-octanoic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 1-(3-Bromo-4-cyclohexyloxy-phenyl)-hexan-2-one (7.08 mmol, 2.5 g), oxo-acetic acid ethyl ester solution in toluene (2.8 mL, 50% solution in toluene) and triethylamine (0.5 mL) was stirred at ambient temperature for 16 h. The reaction mixture was diluted with DCM (300 mL), washed with water (3×100 mL), dried the organic layer and concentrated under reduced pressure. The resultant residue was purified by flash silica gel chromatography using mixture of hexanes in ethyl acetate (9:1) to provide 3-(3-bromo-4-cyclohexyloxy-phenyl)-2-hydroxy-4-oxo-octanoic acid ethyl ester (2.0 g).

Workup

  1. washwashed with water (3×100 mL)
  2. customdried the organic layer
  3. concentrationconcentrated under reduced pressure
  4. customThe resultant residue was purified by flash silica gel chromatography
  5. additionmixture of hexanes in ethyl acetate (9:1)

Sources & evidence

ORD record
ord-3f0e28688d4b4c4080e09a7a0e3f0c89
Source dataset
uspto-grants-2014_06
Patent number
US08741900B2

Reaction notes

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