Hydrochloric Acid → HCID 53662755, compound

HRID 2260429Notes

Reaction equation

HRID 2260429 reaction equation
[BH4-].[Na+].[CH3:3][C:4]([C:7]1[CH:8]=[C:9]([S:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][C:19]2=[O:24])[CH:10]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:12]=1)([CH3:6])[CH3:5].Cl.O>CO>[CH3:16][C:13]([C:11]1[CH:10]=[C:9]([S:17][C@H:18]2[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]2[OH:24])[CH:8]=[C:7]([C:4]([CH3:3])([CH3:5])[CH3:6])[CH:12]=1)([CH3:14])[CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 19000467HCID 19000467, compound

Product 1

HCID 53662755HCID 53662755, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.40 g, 0.0105 mole) was added to a cold (3° C.) solution of 2-[[3,5-bis(1,1-dimethylethyl)phenyl]thio]cyclohexanone (3.18 g, 0.0100 mole) in methanol (150 mL). After 1 hour, 10% hydrochloric acid (5 mL) and water (50 mL) were added. The methanol was removed by rotary evaporator and the title products were extracted into ethyl acetate. The combined extracts were dried over sodium sulfate, filtered and concentrated to an oil. Silica gel chromatography separated the two title products. The major product (first off) was identified as the "cis" product by NMR.

Workup

  1. customThe methanol was removed by rotary evaporator
  2. extractionthe title products were extracted into ethyl acetate
  3. dry with materialThe combined extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to an oil
  6. customSilica gel chromatography separated the two title products

Sources & evidence

ORD record
ord-8d87bac14d3d401b843c27059ff243dd
Source dataset
uspto-grants-1995_12
Patent number
US05476944

Reaction notes

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