Dimethylformamide → 5-Dodecylthiophene-2-carbaldehyde

HRID 1196802

Reaction equation

CN(C)[CH:3]=[O:4].O=P(Cl)(Cl)Cl.[CH2:11]([C:23]1[S:24][CH:25]=[CH:26][CH:27]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>O>[CH2:11]([C:23]1[S:24][C:25]([CH:3]=[O:4])=[CH:26][CH:27]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

Conditions

Temperature: 5 °C

Procedure

In a 1 liter-four-necked flask, 93.7 (1.28 mol) of N,N-dimethylformamide was placed and cooled to 5° C., followed by addition of 107.4 g (7.00×10-1 mol) of POCl3 in 15 min. below 10° C. under stirring. After stirring for 30 min. below 10° C., 160 g (6.35×10-1 mol) of 2-dodecylthiophene was added dropwise to the mixture in 10 min. at room temperature, followed by stirring for 1.5 hours and further stirring for 2.5 hours at 60° C. After the reaction, the reaction mixture was poured into 2 liters of iced water, subjected to 3 times of extraction with 500 ml of chloroform and washed 6 times with 500 ml of water. The organic layer was dried on CaCl2, followed by distilling-off of the solvent to obtain 237 g of a crude product. The crude product was subjected to reduced-pressure distillation in an atmosphere of nitrogen to obtain 135 g of a product (yield: 75.9%). b.p.: 160° C./0.6 mmHg

Workup

stirringAfter stirring for 30 min. below 10° C.
stirringby stirring for 1.5 hours
stirringfurther stirring for 2.5 hours at 60° C
customAfter the reaction
extractionsubjected to 3 times of extraction with 500 ml of chloroform
washwashed 6 times with 500 ml of water
customThe organic layer was dried on CaCl2
customto obtain 237 g of a crude product
distillationThe crude product was subjected to reduced-pressure distillation in an atmosphere of nitrogen

Sources & evidence

ORD record: ord-82136c440a0048babfec4f68af1cc474
Source dataset: uspto-grants-1992_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05116530

Linked notes

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