Ammonium Chloride → (S)-(-)-4,4,4-Trifluoro-3-hydroxy-3-methyl-1-(4-phenylsulfonylphenyl)-trans-but-1-ene

HRID 35891Notes

Reaction equation

HRID 35891 reaction equation
[F:1][C:2]([F:25])([F:24])[C@@:3]([CH3:23])([OH:22])[CH:4](O)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:8][CH:7]=1.OC(C)(C(F)(F)F)C(=O)CC1C=CC(S(C2C=CC=CC=2)(=O)=O)=CC=1.[BH4-].[Na+].[NH4+].[Cl-]>CO>[F:25][C:2]([F:1])([F:24])[C@:3]([OH:22])([CH3:23])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[CH:8][C:9]([S:12]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)(=[O:14])=[O:13])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 19939314HCID 19939314, compoundHCID 57137960(2S)-1,1,1-Trifluoro-2-methyl-4-(4-phenylsulfonylphenyl)-2,3-butanediol

Product 1

HCID 67708369(S)-(-)-4,4,4-Trifluoro-3-hydroxy-3-methyl-1-(4-phenylsulfonylphenyl)-trans-but-1-ene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2S)-1,1,1-Trifluoro-2-methyl-4-(4-phenylsulfonylphenyl)-2,3-butanediol. To a stirred, cooled 0° C. solution of 3-hydroxy-3-methyl-1-(4-phenylsulfonylphenyl)-4,4,4-trifluoro-2-butanone (3.7 g, 10 mmol) in 135 mL methanol was added NaBH4 (1.7 g, 44 mmol). The mixture was stirred for 15 minutes. 100 mL of saturated aqueous NH4Cl was added. The mixture was extracted with dichloromethane and the combined organic layers were dried and evaporated. The resulting solid was pre-absorbed onto silica gel and purified by chromatography, with ether:hexane as the eluent (75:25), to give the title compound as a mixture of isomers (3.13 g, 83%); NMR (CDCl3): 7.96-7.89 (m,4, Ar), 7.58-7.49 (m,3, Ar), 7.48-7.39 (d,2, Ar), 3.91-3.86 (m,2), 3.13 (s,1), 3.08 (s,1), 2.80 (s,1), 2.76-2.75 (d,1), 2.68 (s,1), 1.47 (s,3, CH3); MS: m/z=375(M+1).

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. customthe combined organic layers were dried
  3. customevaporated
  4. customThe resulting solid was pre-absorbed onto silica gel
  5. custompurified by chromatography, with ether

Sources & evidence

ORD record
ord-ba261498cc284b2f81434134316e6102
Source dataset
uspto-grants-1995_05
Patent number
US05411973

Reaction notes

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