Dimethylformamide → Methyl 4-chloro-3-methyl-4-oxobutanoate

HRID 1615686Notes

Reaction equation

HRID 1615686 reaction equation
[CH3:1][O:2][C:3](=[O:10])[CH2:4][CH:5]([CH3:9])[C:6](O)=[O:7].CN(C=O)C.C(Cl)(=O)C([Cl:19])=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:10])[CH2:4][CH:5]([CH3:9])[C:6]([Cl:19])=[O:7]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 45639014-Methoxy-2-methyl-4-oxobutanoic acid

Product 1

HCID 14403282Methyl 4-chloro-3-methyl-4-oxobutanoateYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methoxy-2-methyl-4-oxobutanoic acid (1.2 g, 8.2 mmol) in oxalyl dichloride (15 mL) and DCM (15 mL) was added DMF (20 mg). The mixture was stirred at room temperature for 2 h. The mixture was concentrated to dryness to give the product as a yellow solid (1.3 g, 96% yield). 1H NMR (400 MHz, CDCl3): δ 3.71 (s, 3H), 3.35-3.30 (m, 1H), 2.87 (d, J=8.0 Hz, 0.5H), 2.82 (d, J=8.0 Hz, 0.5H), 2.56 (d, J=5.6 Hz, 0.5H), 2.52 (d, J=5.6 Hz, 0.5H), 1.37 (d, J=7.2 Hz, 3H).

Workup

  1. concentrationThe mixture was concentrated to dryness

Sources & evidence

ORD record
ord-77291be21abd48aa94536eb2576c0a44
Source dataset
uspto-grants-2014_07
Patent number
US08765760B2

Reaction notes

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