Dimethyl malonate → Dimethyl [(dimethylamino)methylidene]propanedioate

HRID 1619379Notes

Reaction equation

HRID 1619379 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[CH3:10][N:11]([CH:13](OC)OC)[CH3:12]>>[CH3:10][N:11]([CH:13]=[C:2]([C:1]([O:8][CH3:9])=[O:7])[C:3]([O:5][CH3:6])=[O:4])[CH3:12]

Participants

3

Reactant 2

HCID 7943Dimethyl malonateHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 593603Dimethyl [(dimethylamino)methylidene]propanedioateYield 98.7%

Procedure

A solution of dimethyl malonate (5 g, 37.9 mmol, 1 equiv) in DMF-DMA (11.3 g, 94.8 mmol, 2.5 equiv) was stirred at room temperature overnight. Then the reaction mixture was concentrated to give 7 g of the desired product, which was directly used for the next step without further purification. MS (ESI): 188 (MH+).

Workup

  1. concentrationThen the reaction mixture was concentrated

Sources & evidence

ORD record
ord-7434af8fe5bc478882cbb6e406ca2e18
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

Loading…