Ethyl bromoacetate → 4-(4-Methoxy-phenyl)-4-oxo-3-phenyl-butyric acid ethyl ester

HRID 221806

Reaction equation

HRID 221806 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:19])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][CH:6]=1.Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>CS(C)=O.C1(C)C=CC=CC=1>[CH2:25]([O:24][C:22](=[O:23])[CH2:21][CH:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:11]([C:8]1[CH:7]=[CH:6][C:5]([O:4][CH3:3])=[CH:10][CH:9]=1)=[O:19])[CH3:26]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 2310931-(4-Methoxyphenyl)-2-phenylethan-1-one

Product 1

HCID 134415094-(4-Methoxy-phenyl)-4-oxo-3-phenyl-butyric acid ethyl esterYield 99%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 1140TolueneSolvent2×

Procedure

A suspension of NaH (12.8 mmol, 512 mg) in DMSO (23 mL) was added 4′-methoxy-2-phenylacetophenone (12.8 mmol, 2.89 g) in 10 ml toluene dropwise under argon. After 30 minutes of stirring, ethyl bromoacetate (1.4 mL, 1 eq.) in 10 mL of toluene was added and the mixture was stirred at rt overnight. The reaction was quenched by addition of 2N HCl (4 mL), and then 60 mL of water. The mixture was extracted with CH2Cl2 (3×30 mL), dried over MgSO4 and concentrated under vacuum overnight to afforded 4.0 g (99%) of 4-(4-methoxy-phenyl)-4-oxo-3-phenyl-butyric acid ethyl ester.

Workup

  1. stirringthe mixture was stirred at rt overnight
  2. customThe reaction was quenched by addition of 2N HCl (4 mL)
  3. extractionThe mixture was extracted with CH2Cl2 (3×30 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under vacuum overnight

Sources & evidence

ORD record
ord-d5dede9e60234ccd97e8138e4cd87ad3
Source dataset
uspto-grants-2012_06
Patent number
US08207168B2

Linked notes

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