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Pyridine → HCID 71014114, compound

HRID 240875
Notes
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Reaction equation

HRID 240875 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

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

Product 1

HCID 71014114HCID 71014114, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6344Dichloromethane
Solvent
HCID 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-7329a17e954a4611b504b44bb517cca8
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08648081B2

Reaction notes

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