Oxalyl chloride → (E)-4-(diMethylaMino)but-2-enoyl chloride
Reaction equation
[ClH:1].[CH3:2][N:3]([CH3:10])[CH2:4]/[CH:5]=[CH:6]/[C:7](O)=[O:8].C(Cl)(=O)C([Cl:14])=O>C1COCC1.CN(C=O)C>[ClH:14].[CH3:2][N:3]([CH3:10])[CH2:4]/[CH:5]=[CH:6]/[C:7]([Cl:1])=[O:8]Participants
5
Conditions
- Temperature
- 22.5 °C
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.
Workup
- temperaturethen cooled to 0° C.
- waitheld for 30 min
- customThe solids were collected on Buchner funnel (under a blanket of nitrogen) and
- washwashed with cold (0° C.) THF (3×5 mL)
- customThe product was dried under vacuum (˜1 torr) at 40-50 2° C. for 3 h
Sources & evidence
- ORD record
- ord-d80a9145758845abb1fa8eb24515b6b4
- Source dataset
- uspto-grants-2010_04
- Patent number
- USRE041253E1
Reaction notes
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