Sodium Hydroxide → HCID 71472638, compound

HRID 1773812Notes

Reaction equation

HRID 1773812 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]

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 887MethanolSolventHCID 962WaterSolvent

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-f75ed8c449ba449dba9c9dcfe1050211
Source dataset
uspto-grants-2016_02
Patent number
US09255111B2

Reaction notes

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