Dimethyl malonate → HCID 86612768, compound

HRID 2221368Notes

Reaction equation

[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].C[O-].[Na+].[N:13]([CH2:16][Si:17]([O:21][CH3:22])([O:19][CH3:20])[CH3:18])=[C:14]=[O:15]>>[CH3:20][O:19][Si:17]([CH2:16][NH:13][C:14]([CH:2]([C:1]([O:8][CH3:9])=[O:7])[C:3]([O:5][CH3:6])=[O:4])=[O:15])([O:21][CH3:22])[CH3:18]

Participants

Reactant 3

HCID 7943Dimethyl malonate

HCID 10942334Sodium Methoxide

HCID 17959832(Isocyanatomethyl)(dimethoxy)methylsilane

Product 1

HCID 86612768HCID 86612768, compoundYield 56%

Procedure

A stirred mixture conditioned at a temperature of 30° C. of 6.74 g of dimethyl malonate and 90.0 mg of sodium methoxide (30% strength solution in methanol) was admixed dropwise with 8.06 g of (isocyanatomethyl)-dimethoxy(methyl)silane and the clear solution was stirred for 90 min. This gave dimethyl 2-{[dimethoxy(methyl)silyl]methylcarbamoyl}malonate after recrystallization from isohexane in 56% yield with a purity of >95% (analysis by 1H NMR).

Workup

customThis gave dimethyl 2-{[dimethoxy(methyl)silyl]methylcarbamoyl}malonate after recrystallization from isohexane in 56% yield with a purity of >95% (analysis by 1H NMR)

Sources & evidence

ORD record: ord-b4110bacb678402ea80b86f294aecec7
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368586B2

Reaction notes

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