Methyl acetoacetate → Methyl 2-[(dimethylamino)methylene]acetoacetate

HRID 1488206Notes

Reaction equation

[O:1]=[C:2]([CH3:8])[CH2:3][C:4]([O:6][CH3:7])=[O:5].CO[CH:11]([N:14]([CH3:16])[CH3:15])OC>>[CH3:11][N:14](/[CH:16]=[C:3](/[C:2](=[O:1])[CH3:8])\[C:4]([O:6][CH3:7])=[O:5])[CH3:15]

Participants

Reactant 2

HCID 7757Methyl acetoacetate

HCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 17874501Methyl 2-[(dimethylamino)methylene]acetoacetate

Conditions

Temperature: 80 °C

Procedure

Into a 250-mL round-bottom flask, was placed methyl 3-oxobutanoate (10.8 g, 92.6 mmol) and (dimethoxymethyl)dimethylamine (12.7 mL, 95.3 mmol). The resulting solution was stirred for 2.5 h at 80° C., then concentrated under reduced pressure to yield 14.5 g (crude) of the title compound as a red solid.

Workup

customInto a 250-mL round-bottom flask, was placed
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-63f9962e09584cef8fb23b8ceb188d07
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428502B2

Reaction notes

Loading…