Pyridine → HCID 71014114, compound

HRID 336987Notes

Reaction equation

HRID 336987 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-046dfeb6fc474080ad589bc15f913548
Source dataset
uspto-grants-2014_11
Patent number
US08889710B2

Reaction notes

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