tert-Butoxy bis(dimethylamino)methane → HCID 12836786, compound

HRID 354644Notes

Reaction equation

HRID 354644 reaction equation
[C:1]([O:4]/[CH:5]=[CH:6]/[CH3:7])(=[O:3])[CH3:2].[CH3:8][N:9]([CH:11](N(C)C)OC(C)(C)C)[CH3:10]>>[CH3:8][N:9]([CH3:11])/[CH:10]=[CH:2]/[C:1]([O:4]/[CH:5]=[CH:6]/[CH3:7])=[O:3]

Participants

3

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 637917HCID 637917, compound

Product 1

HCID 12836786HCID 12836786, compoundYield 91%

Procedure

A solution of 20.0 g (0.2 mole) of trans-propenyl acetate and 101.0 g (0.6 mole) of bis(dimethylamino)-tert.-butoxymethane under argon was heated at 50° C. overnight (161/2 hours). The excess reagent was removed by vacuum distillation (0.7 mmHg, oil bath at 50° C.). The residue was chromatographed rapidly on 300 g of silica gel 60 eluting with ethyl acetate/hexane (2:3 parts by volume) to give 28.2 g (91%) of trans-3-(dimethylamino)-2-propenoic acid, trans-propenyl ester which was used in the next step with no further purification. This material was sublimed (to remove yellow color) at 40°-50° C. 0.2 mmHg. The analytical sample was recrystallized from pentane. Mp 48°-48.5° C.

Workup

  1. customThe excess reagent was removed by vacuum distillation (0.7 mmHg, oil bath at 50° C.)
  2. customThe residue was chromatographed rapidly on 300 g of silica gel 60 eluting with ethyl acetate/hexane (2:3 parts by volume)

Sources & evidence

ORD record
ord-f4a5717327b84de3869410cbe48b1298
Source dataset
uspto-grants-1983_03
Patent number
US04376207

Reaction notes

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