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
- 0 °C
Procedure
A well stirred suspension of 4-dimethylaminocrotonic acid hydrochloride (5.0 g, 30 mmol) in cold (0° C.) THF (40 mL) and DMF (2 pipet drops) is treated with oxalyl chloride (3.15 mL, 36 mmol). Stirring at 20–25° C. for 3 hours is followed by cooling to 0° C. and holding for 30 minutes. Solids are collected on a Buchner funnel (under a blanket of nitrogen) and the cake is washed with cold (0° C.) THF (3×5 mL). The solid is dried under vacuum (˜1 torr) at 40–50° C. for 3 hours 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
- stirringStirring at 20–25° C. for 3 hours
- customSolids are collected on a Buchner funnel (under a blanket of nitrogen) and the cake
- washis washed with cold (0° C.) THF (3×5 mL)
- customThe solid is dried under vacuum (˜1 torr) at 40–50° C. for 3 hours
Sources & evidence
- ORD record
- ord-e40b080488a441199aa260fdab6f580a
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07126025B2
Reaction notes
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