Dimethylformamide → 5-Hexylthiophene-2-carboxaldehyde

HRID 892379Notes

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

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%). Then, 20 g of the product obtained was purified by silica gel column chromatography with the use of an n-hexane/ethyl acetate=20/1 mixture solvent to obtain 18.2 g of a pure product (yield: 91.0%).

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-83c65a0ac40a498f840bfdc1c948d57a
Source dataset: uspto-grants-1992_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05118441

Reaction notes

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