tert-Butoxy bis(dimethylamino)methane → 4-(Dimethylamino)-1,1-dimethoxybut-3-en-2-one

HRID 2292565Notes

Reaction equation

HRID 2292565 reaction equation
[CH3:1][O:2][CH:3]([O:7][CH3:8])[C:4]([CH3:6])=[O:5].C(O[CH:14](N(C)C)[N:15]([CH3:17])[CH3:16])(C)(C)C>>[CH3:14][N:15]([CH3:17])[CH:16]=[CH:6][C:4](=[O:5])[CH:3]([O:7][CH3:8])[O:2][CH3:1]

Participants

3

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 80650Pyruvic aldehyde dimethyl acetal

Product 1

HCID 27821454-(Dimethylamino)-1,1-dimethoxybut-3-en-2-one

Procedure

1,1-dimethoxyacetone (pyruvic aldehyde dimethyl acetal, Aldrich Chemical Co.) (3 cm3) was added dropwise with stirring to tert-butoxy-bis(dimethylamino)methane (Fluka Chemie AG) (5 cm3) and stirring continued at ambient temperature for 16 hours. The low-boiling impurities were removed by evaporation under reduced pressure. This left an orange oil (5.82 g) (1H NMR (CDCl3): δ2.88(3H,br s); 3.10(3H,br s); 3.40(6H,s); 4.58(1H,s); 5.34(1H,d); 7.76(1H,d)).

Workup

  1. customThe low-boiling impurities were removed by evaporation under reduced pressure
  2. waitThis left an orange oil (5.82 g) (1H NMR (CDCl3): δ2.88(3H,br s); 3.10(3H,br s); 3.40(6H,s); 4.58(1H,s); 5.34(1H,d); 7.76(1H,d))

Sources & evidence

ORD record
ord-bf14d7544aa74906b2884a5f969f64e7
Source dataset
uspto-grants-1997_11
Patent number
US05684011

Reaction notes

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