Dimethylformamide → 5-Hexylthiophene-2-carboxaldehyde
Reaction equation
CN(C)[CH:3]=[O:4].O=P(Cl)(Cl)Cl.[CH2:11]([C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>O>[CH2:11]([C:17]1[S:18][C:19]([CH:3]=[O:4])=[CH:20][CH:21]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
In a 3 liter-four-necked flask, 173.7 (2.38 mol) of N,N-dimethylformamide was placed and cooled to 5° C., followed by addition of 201.4 g (1.31 mol) of POCl3 in 15 min. below 10° C. under stirring. After stirring for 30 min. below 10° C., 200 g (1.19 mol) of 2-hexylthiophene was added dropwise to the mixture in 10 min. at room temperature, followed by stirring for 1.5 hours and further stirring for 2 hours at 60° C. After the reaction, the reaction mixture was poured into 5 liter of iced water, subjected to 3 times of extraction with 2 liter of chloroform and washed 6 times with 2 liter of water. The organic layer was dried with CaCl2, followed by distilling-off of the solvent and reduced-pressure distillation in an atmosphere of nitrogen to obtain 199.2 g of a product (yield: 85.0%).
Workup
- stirringAfter stirring for 30 min. below 10° C.
- stirringby stirring for 1.5 hours
- stirringfurther stirring for 2 hours at 60° C
- customAfter the reaction
- extractionsubjected to 3 times of extraction with 2 liter of chloroform
- washwashed 6 times with 2 liter of water
- dry with materialThe organic layer was dried with CaCl2
- distillationfollowed by distilling-off of the solvent and reduced-pressure distillation in an atmosphere of nitrogen
Sources & evidence
- ORD record
- ord-2052771e5dc942ed921029e39f63e354
- Source dataset
- uspto-grants-1995_03
- Patent number
- US05395551
Reaction notes
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