Dimethylformamide → HCID 58669199, compound

HRID 1444995Notes

Reaction equation

[CH3:1][C:2]1[C:6]([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)=[CH:5][S:4][CH:3]=1.O=P(Cl)(Cl)Cl.CN([CH:21]=[O:22])C>>[CH:21]([C:3]1[S:4][CH:5]=[C:6]([CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[C:2]=1[CH3:1])=[O:22]

Participants

Reactant 3

HCID 6228Dimethylformamide2×

HCID 24813Phosphorus oxychloride

HCID 15194123-cyclohexyl-4-methylthiophene

Product 1

HCID 58669199HCID 58669199, compoundYield 83%

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-methyl-4-cyclohexylthiophene (3 g, 17 mmol) in DMF (10 mL) was added 10 mL of a solution prepared from DMF and POCl3 (4:1, v:v). The temperature was maintained at about 0° C. during the addition. The reaction mixture was then stirred overnight at room temperature, and poured into ice water. After neutralization with 25% NaOH solution to pH˜8, the product was extracted with dichloromethane. The solvent was evaporated to afford the crude product 2-formyl-3-methyl-4-cyclohexylthiophene as a solid which was purified by column chromatography (dichloromethane-petroleum ether (1:3)) (2.85 g, yield: 83%). 1H NMR (CDCl3) δ 10.07 (s, 1, CHO), 7.28 (s, 1, thienyl-H), 2.58 (m,1,cyclohexyl methane), 2.53 (s, 3,CH3),1.89 and 1.37 m, 10, cyclohexyl).

Workup

extractionAfter neutralization with 25% NaOH solution to pH˜8, the product was extracted with dichloromethane
customThe solvent was evaporated

Sources & evidence

ORD record: ord-08c2a8c0cb3f4d6f87c177b17648c8f3
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07663301B2

Reaction notes

Loading…