Pyridine → 3-[3-(3,5-Dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-but-2-enoyl]-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylic acid methyl ester

HRID 240901Notes

Reaction equation

HRID 240901 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:13](=[O:30])[CH2:14][C:15]([C:21]2[CH:26]=[C:25]([Cl:27])[C:24]([F:28])=[C:23]([Cl:29])[CH:22]=2)(O)[C:16]([F:19])([F:18])[F:17])=[C:8]2[CH2:12][CH2:11][CH2:10][C:9]=12)=[O:4].O=S(Cl)Cl.N1C=CC=CC=1>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:13](=[O:30])[CH:14]=[C:15]([C:21]2[CH:26]=[C:25]([Cl:27])[C:24]([F:28])=[C:23]([Cl:29])[CH:22]=2)[C:16]([F:19])([F:18])[F:17])=[C:8]2[CH2:12][CH2:11][CH2:10][C:9]=12)=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 866937483-[3-(3,5-Dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-3-hydroxy-butyryl]-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylic acid methyl ester

Product 1

HCID 866937493-[3-(3,5-Dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-but-2-enoyl]-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylic acid methyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Stir a mixture of 3-[3-(3,5-Dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-3-hydroxyl-butyryl]-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylic acid methyl ester (26 g, 53.7 mmol), SOCl2 (12.7 g, 7.8 mL, 0.107 mmol) and pyridine (42.3 g, 0.537 mmol) in anhydrous DCM (300 mL) at room temperature for 3 hours. Concentrate the mixture under vacuum. Purify the residue by silica gel chromatograph (PE:EtOAc 12:1) to afford 3-[3-(3,5-Dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-but-2-enoyl]-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylic acid methyl ester as a pale yellow solid (25 g, 100%). (m/z): 467 (M+1).

Workup

  1. concentrationConcentrate the mixture under vacuum
  2. customPurify the residue by silica gel chromatograph (PE:EtOAc 12:1)

Sources & evidence

ORD record
ord-7d78e22a484f4422aacff13026165b67
Source dataset
uspto-grants-2014_02
Patent number
US08648081B2

Reaction notes

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