Diethyl Oxalate → Ethyl (3-methoxyphenyl)pyruvate

HRID 1508429Notes

Reaction equation

HRID 1508429 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].[CH3:16][O:17]C1C=C(C=CC=1)CBr.[Mg].C(OCC)(=O)C(OCC)=O>>[CH3:16][O:17][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 40672073-Methoxybenzyl bromideHCID 5462224MagnesiumHCID 18370709Ethyl (2-fluorophenyl)pyruvate

Product 1

HCID 18370264Ethyl (3-methoxyphenyl)pyruvateYield 74%

Procedure

The title compound was prepared as described for B4 using 3-methoxybenzyl bromide (1.5 g, 7.46 mmol), magnesium (0.199 g, 8.21 mmol) and diethyl oxalate (2.18 g, 14.92 mmol). The product was isolated in the form of colorless oil in 74% yield and used instantly in next step.

Workup

  1. customThe product was isolated in the form of colorless oil in 74% yield

Sources & evidence

ORD record
ord-6e50e5f6f09c43fbac72a8d3d4cdacfb
Source dataset
uspto-grants-2015_12
Patent number
US09221860B2

Reaction notes

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