Pyridine → HCID 71014114, compound

HRID 1773811Notes

Reaction equation

HRID 1773811 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](O)([C:26]([F:29])([F:28])[F:27])[CH2:10][C:11]([C:13]2[S:17][C:16]([C:18]([O:20][CH3:21])=[O:19])=[C:15]3[CH2:22][CH2:23][CH2:24][CH2:25][C:14]=23)=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1.O=S(Cl)Cl.N1C=CC=CC=1>C(Cl)Cl.[NH4+].[Cl-]>[CH3:21][O:20][C:18]([C:16]1[S:17][C:13]([C:11](=[O:12])[CH:10]=[C:9]([C:4]2[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=2)[C:26]([F:29])([F:28])[F:27])=[C:14]2[CH2:25][CH2:24][CH2:23][CH2:22][C:15]=12)=[O:19]

Participants

6

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 71014111Methyl 3-[3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxy-1-oxobutyl]-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxylate

Product 1

HCID 71014114HCID 71014114, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

Stir a mixture of methyl 3-(3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxyl butanoyl)-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxylate (9.1 g, 18.9 mmol), SOCl2 (9.0 g, 5.5 mL, 75.6 mmol) and pyridine (2.99 g, 3.1 mL, 37.8 mmol) in anhydrous DCM (100 mL) at ambient temperature overnight. Dilute the resultant mixture with saturated NH4Cl aqueous solution. Extract the aqueous mixture with DCM (100 mL×3). The combined organic layers are washed with brine, dried over anhydrous Na2SO4 and concentrated under vacuum. Purify the residue by silica gel chromatograph (PE:EtOAc 50:1) to afford 3-[3-(3,5-Dichloro-phenyl)-4,4,4-trifluoro-but-2-enoyl]-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid methyl ester as an orange solid (8.75 g, 100%). (m/z): 463 (M+1).

Workup

  1. extractionExtract the aqueous mixture with DCM (100 mL×3)
  2. washThe combined organic layers are washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under vacuum
  5. customPurify the residue by silica gel chromatograph (PE:EtOAc 50:1)

Sources & evidence

ORD record
ord-bbf5d1b818b84768ac82349cf7020745
Source dataset
uspto-grants-2016_02
Patent number
US09255111B2

Reaction notes

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