Diethyl Oxalate → Ethyl (3-methylphenyl)pyruvate

HRID 1508441Notes

Reaction equation

HRID 1508441 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]C1C=C(C=CC=1)CBr.[Mg].C(OCC)(=O)C(OCC)=O>>[CH3:16][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 12099m-Xylyl bromideHCID 5462224MagnesiumHCID 18370709Ethyl (2-fluorophenyl)pyruvate

Product 1

HCID 18370163Ethyl (3-methylphenyl)pyruvateYield 72%

Procedure

The title compound was prepared as described for B4 using 3-methylbenzyl bromide (1.250 g, 6.75 mmol), magnesium (0.181 g, 7.43 mmol) and diethyl oxalate (1.974 g, 13.51 mmol). The resulting compound was isolated in the form of colorless oil in 72% yield and use instantly in next step.

Workup

  1. customThe resulting compound was isolated in the form of colorless oil in 72% yield and use instantly in next step

Sources & evidence

ORD record
ord-70fa1adfca2e47cea4bccfcb37332589
Source dataset
uspto-grants-2015_12
Patent number
US09221860B2

Reaction notes

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