Diethyl Oxalate → Ethyl (3-trifluoromethylphenyl)pyruvate

HRID 1508431Notes

Reaction equation

HRID 1508431 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9](=[O:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11].[F:16][C:17]([F:27])([F:26])C1C=C(C=CC=1)CBr.[Mg].C(OCC)(=O)C(OCC)=O>>[F:16][C:17]([F:27])([F:26])[C:7]1[CH:2]=[C:3]([CH2:8][C:9](=[O:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 4

HCID 7268Diethyl OxalateHCID 1230611-(Bromomethyl)-3-(trifluoromethyl)benzeneHCID 5462224MagnesiumHCID 18370709Ethyl (2-fluorophenyl)pyruvate

Product 1

HCID 18370921Ethyl (3-trifluoromethylphenyl)pyruvateYield 78%

Procedure

The title compound was prepared as described for B4 using 3-trifluoromethylbenzyl bromide (2.5 g, 10.46 mmol), magnesium (0.280 g, 11.50 mmol) and diethyl oxalate (3.06 g, 20.92 mmol). The product was isolated in the form of colorless oil in 78% yield and use instantly in next step.

Workup

  1. customThe product was isolated in the form of colorless oil in 78% yield and use instantly in next step

Sources & evidence

ORD record
ord-cd899ce840084fc7a4219fce2c639eb4
Source dataset
uspto-grants-2015_12
Patent number
US09221860B2

Reaction notes

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