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Sodium Hydroxide → HCID 71472638, compound

HRID 336988
Notes
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Reaction equation

HRID 336988 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:14](=O)[CH:15]=[C:16]([C:21]2[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=2)[C:17]([F:20])([F:19])[F:18])=[C:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=12)=[O:4].[OH-:30].[Na+].[NH2:32]O.Cl>CO.O>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:14]2[CH2:15][C:16]([C:21]3[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=3)([C:17]([F:20])([F:19])[F:18])[O:30][N:32]=2)=[C:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=12)=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 71014114HCID 71014114, compound

Product 1

HCID 71472638HCID 71472638, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 962
Water
Solvent

Procedure

Stir a mixture of 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 (8.75 g, 18.9 mmol), NaOH (2.65 g, 66.1 mmol) and NH2OH—HCl (2.6 g, 37.8 mmol) in MeOH (60 mL) and water (15 mL) at room temperature for 2.5 hour. After removal of solvent under vacuum, dilute the residue with ice water (50 mL). Acidify the aqueous mixture with conc. HCl to pH=1 and extract the resultant mixture with EtOAc (50 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-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid methyl ester as an orange solid (8.1 g, 93.1%). MS (m/z): 478 (M+1).

Workup

  1. customAfter removal of solvent under vacuum
  2. additiondilute the residue with ice water (50 mL)
  3. extractionextract the resultant mixture with EtOAc (50 mL×3)
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under vacuum
  7. customPurify the residue by silica gel chromatograph (PE:EtOAc 50:1)

Sources & evidence

ORD record
ord-b7a9a5625f7144988af2a50f9db467c0
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08889710B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes