1-(3-(Bromomethyl)phenyl)ethan-1-one → Ethyl 2-(3-acetylbenzyl)-3-oxobutanoate

HRID 1718277Notes

Reaction equation

HRID 1718277 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7]Br)(=[O:3])[CH3:2].[Na].[C:13]([O:19][CH2:20][CH3:21])(=[O:18])[CH2:14][C:15]([CH3:17])=[O:16]>O1CCCC1>[C:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7][CH:14]([C:15](=[O:16])[CH3:17])[C:13]([O:19][CH2:20][CH3:21])=[O:18])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 154798071-(3-(Bromomethyl)phenyl)ethan-1-oneHCID 87089461Ethyl acetoacetatesodium salt

Product 1

HCID 57460081Ethyl 2-(3-acetylbenzyl)-3-oxobutanoateYield 49.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-acetylbenzyl bromide (4 g) and ethyl acetoacetate sodium salt (3.42 g) in tetrahydrofuran (50 mL) was stirred for 12 hr. The insoluble material was filtered off and the filtrate was concentrated. The residue was purified by silica gel column chromatography to give the title compound (2.42 g, 49%) as a colorless viscous oil.

Workup

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-42a260483dfb47128689a80a7519fc03
Source dataset
uspto-grants-2010_09
Patent number
US07803940B2

Reaction notes

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