Ethyl ketone → 1-(Dimethylamino)-2-methylpent-1-en-3-one

Diethyl ketone (29.71 g; 0.345 mol) and [3-(dimethylamino)-2-azaprop-2-en-1-ylidene]dimethyl-ammonium chloride (37.64 g; 0.230 mol) were added to a solution of 30% of sodium methoxide in methanol (41.41 g; 0.230 mol) and methanol (305 ml) at 20° C. under N2. The reaction mixture was refluxed for 18 h and then concentrated under reduced pressure. The residue was dissolved in dichloromethane (300 ml) and washed with saturated sodium bisulphite solution (3×100 ml). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. This gave 26.60 g of product, which comprised 42% by weight of 1-(dimethylamino)-2-methylpent-1-en-3-one (corresponding to a yield of 34%).

1. temperatureThe reaction mixture was refluxed for 18 h
2. concentrationconcentrated under reduced pressure
3. dissolutionThe residue was dissolved in dichloromethane (300 ml)
4. washwashed with saturated sodium bisulphite solution (3×100 ml)
5. dry with materialThe organic phase was dried over Na2SO4
6. concentrationconcentrated under reduced pressure

ORD record

ord-d3065b1982df4f78b2229d5dbd5f158d

Source dataset

uspto-grants-2004_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06689918B2