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

HRID 1673605Notes

Reaction equation

HRID 1673605 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-80deb4ce116f4a2ca83522051f2b0db0
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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