Phenacyl bromide → Ethyl 2-cyano-4-oxo-4-phenylbutanoate

HRID 339724Notes

Reaction equation

HRID 339724 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[H-].[Na+].Br[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:14]>O1CCCC1>[C:1]([CH:3]([CH2:12][C:13](=[O:14])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2]

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 7764Ethyl cyanoacetateHCID 24758Sodium hydride

Product 1

HCID 15633746Ethyl 2-cyano-4-oxo-4-phenylbutanoateYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of ethyl 2-cyanoacetate (10 g, 88.4 mmol) in tetrahydrofuran (50 ml) at 0° C. was added sodium hydride (4.2 g, 60% in mineral oil, 105 mmol) portionly. The reaction mixture was stirred for 30 minutes, and 2-bromoacetophenone (20 g, 100 mmol) in tetrahydrofuran (20 ml) was added dropwisely. After warming the mixture to room temperature, it was stirred for 4 hours. The resulting solution was quenched with water and normal work-up accomplished with diethyl ether. The organic layer was dried with MgSO4, and purified by silica gel column chromatography (EtOAc:Hx=1:3) to produce desired compound (19 g, 98%) as light yellow color oil.

Workup

  1. stirringit was stirred for 4 hours
  2. customThe resulting solution was quenched with water and normal work-up
  3. dry with materialThe organic layer was dried with MgSO4
  4. custompurified by silica gel column chromatography (EtOAc:Hx=1:3)

Sources & evidence

ORD record
ord-822d8145ff184a5d9dcfeaf7272c5372
Source dataset
uspto-grants-2014_11
Patent number
US08895558B2

Reaction notes

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