1-Acetoxy-2-bromoethane → Diethyl alpha-phenyl-alpha-(2-acetoxyethyl)malonate

HRID 1780211Notes

Reaction equation

HRID 1780211 reaction equation
CC(C)([O-])C.[K+].[C:7]1([CH:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:24]([O:27][CH2:28][CH2:29]Br)(=[O:26])[CH3:25]>CN(C=O)C.O>[C:7]1([C:13]([CH2:29][CH2:28][O:27][C:24](=[O:26])[CH3:25])([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 135641-Acetoxy-2-bromoethaneHCID 66514Diethyl phenylmalonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 19050130Diethyl alpha-phenyl-alpha-(2-acetoxyethyl)malonateYield 100.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of potassium tert.butoxide (448 g, 4M) in DMF (2 l) under nitrogen at room temperature was treated dropwise with diethyl phenylmalonate (945 g, 4M). 1-Acetoxy-2-bromoethane (668 g, 4M) was added. The reaction was allowed to cool to room temperature after 45 mins and was diluted with water (5 l) then extracted with IPE (2 l, 500 ml). The extracts were washed, dried and evaporated to give the title compound (1300 g). Bp 130°/0.05 mm.

Workup

  1. extractionthen extracted with IPE (2 l, 500 ml)
  2. washThe extracts were washed
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-5b09261e40aa4a84aeb5d54b71602beb
Source dataset
uspto-grants-1997_05
Patent number
US05629432

Reaction notes

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