Reaction #833506

Reaction equation

4-dimethylaminocrotonic acid hydrochloride

oxalyl chloride

→

4-dimethylaminocrotonoyl chloride hydrochloride

Yield 72.4%

Solvents

THF

DMF

Conditions

Workup

1. 1
   Temperaturethen cooled to 0° C.
2. 2
   workup.WAITheld for 30 min
3. 3
   OtherThe solids were collected on Buchner funnel (under a blanket of nitrogen) and
4. 4
   Washwashed with cold (0° C.) THF (3×5 mL)
5. 5
   OtherThe product was dried under vacuum (˜1 torr) at 40-50 2° C. for 3 h

Procedure

A well stirred suspension 4-dimethylaminocrotonic acid hydrochloride (5.0 g, 30 mmol) in cold (0° C.) THF (40 mL) and DMF (2 pipet drops) was treated with oxalyl chloride (3.15 mL, 36 mmol). The mixture was stirred at 20-25° C. for 3 h then cooled to 0° C. and held for 30 min. The solids were collected on Buchner funnel (under a blanket of nitrogen) and washed with cold (0° C.) THF (3×5 mL). The product was dried under vacuum (˜1 torr) at 40-50 2° C. for 3 h to give 4.0 g of 4-dimethylaminocrotonoyl chloride hydrochloride. This material is characterized as its methyl ester by treatment of the solid with methanol.

Source