Hydrochloric Acid → HCID 178521546, compound

HRID 726503Notes

Reaction equation

HRID 726503 reaction equation
[BH4-].[Na+].Cl.[F:4][C:5]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:6]=1[C:12]1[CH2:17][CH2:16][CH:15]([CH:18]2[CH2:23][CH2:22][C:21](=[O:24])[CH2:20][CH2:19]2)[CH2:14][CH:13]=1>>[F:4][C:5]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:6]=1[C:12]1[CH2:17][CH2:16][CH:15]([C@H:18]2[CH2:19][CH2:20][C@H:21]([OH:24])[CH2:22][CH2:23]2)[CH2:14][CH:13]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 19706374HCID 19706374, compound

Product 1

HCID 178521546HCID 178521546, compoundYield 80.9%

Procedure

First, 100 ml of a mixed solvent (methanol/tetrahydrofuran=1/7) and 1.5 g of sodium borohydride were placed in a 300 ml flask. Then, a solution in which 5.65 g of 4-[4-(2,3-difluorophenyl)-3-cyclohexenyl]cyclohexanone was dissolved in 80 ml of a mixed solvent (methanol/tetrahydrofuran=1/7) was added dropwise to the mixture at -25° C. The mixture was allowed to warm to room temperature and stirred for 6 hours. Thereafter, diluted hydrochloric acid was added to the reaction mixture, and an organic layer was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away. The residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=3/1) to obtain 4.6 g of trans-4-[4-(2,3-difluorophenyl)-3-cyclohexenyl]cyclohexanol (Y: 80.7%). The compound thus obtained had a purity of 99.3% by GC.

Workup

  1. additionwas added dropwise to the mixture at -25° C
  2. extractionan organic layer was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThereafter, the solvent was distilled away
  6. customThe residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-da8bbda454994d6aa25f5904b98f8584
Source dataset
uspto-grants-1998_01
Patent number
US05709911

Reaction notes

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