Lithium hydroxide, monohydrate → HCID 71471630, compound

HRID 1773813Notes

Reaction equation

HRID 1773813 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:14]2[CH2:18][C:17]([C:23]3[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[CH:24]=3)([C:19]([F:22])([F:21])[F:20])[O:16][N:15]=2)=[C:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=12)=[O:4].O[Li].O>CO.O>[Cl:30][C:25]1[CH:24]=[C:23]([C:17]2([C:19]([F:20])([F:22])[F:21])[O:16][N:15]=[C:14]([C:7]3[S:6][C:5]([C:3]([OH:4])=[O:2])=[C:9]4[CH2:10][CH2:11][CH2:12][CH2:13][C:8]=34)[CH2:18]2)[CH:28]=[C:27]([Cl:29])[CH:26]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 71472638HCID 71472638, compound

Product 1

HCID 71471630HCID 71471630, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Stir a mixture of 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 (8.1 g, 17.0 mmol) and LiOH—H2O (3.57 g 84.9 mmol) in MeOH (64 mL) and water (16 mL) at room temperature overnight. After removal of organic solvent under vacuum, dilute the residue with ice water (80 mL). Acidify the aqueous mixture with conc. HCl to pH=1, and extract the resultant mixture with EtOAc (100 mL×3). The combined organic layers are washed brine, dried over anhydrous Na2SO4 and concentrated under vacuum. Purify the residue by silica gel chromatograph (PE:EtOAc 1:1) 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 as pale yellow solid (6.8 g, 86.4%). MS (m/z): 464 (M+1).

Workup

  1. customAfter removal of organic solvent under vacuum
  2. additiondilute the residue with ice water (80 mL)
  3. extractionextract the resultant mixture with EtOAc (100 mL×3)
  4. washThe combined organic layers are washed brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under vacuum
  7. customPurify the residue by silica gel chromatograph (PE:EtOAc 1:1)

Sources & evidence

ORD record
ord-a3f37ae5a6ba455db3080e043d920ba1
Source dataset
uspto-grants-2016_02
Patent number
US09255111B2

Reaction notes

Loading…