Water → HCID 23440380, compound

HRID 2119282Notes

Reaction equation

HRID 2119282 reaction equation
[CH2:1]([CH:5]1[CH2:10][CH2:9][CH:8]([CH:11]2[CH2:16][CH2:15][C:14]([CH:17]3[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]3)=[CH:13][CH2:12]2)[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].[BH4-].[Na+].O>C(O)C>[CH2:1]([CH:5]1[CH2:6][CH2:7][CH:8]([CH:11]2[CH2:16][CH2:15][C:14]([CH:17]3[CH2:18][CH2:19][CH:20]([OH:23])[CH2:21][CH2:22]3)=[CH:13][CH2:12]2)[CH2:9][CH2:10]1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 23440387HCID 23440387, compound

Product 1

HCID 23440380HCID 23440380, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

In 50 ml of ethanol was dissolved 4.0 g (13 mmol) of the 4-(4-(4-n-butylcyclohexyl)-1-cyclohexenyl)cyclohexanone described above, and the solution was cooled down to 0° C. Sodium borohydride in an amount of 0.25 g (6.6 mmol) was gradually added thereto such that the liquid temperature did not exceed 15° C., and the mixture was stirred for 1 hour. Water in an amount of 50 ml was added to the reaction solution, the product thus formed was extracted with ether, the extract was washed with 1N hydrochloric acid and water in this turn, and then the solvent was distilled off. After the residue was purified by column chromatography on silica gel (eluent: heptane/ethyl acetate=3/1), the solvent was distilled off. The residue was recrystallized from ethanol to give 1.6 g (5.0 mmol) of 4-(4-(4-n-butylcyclohexyl)-1-cyclohexenyl)cyclohexanol. Yield of this compound based on 4-(4-(4-n-butylcyclohexyl)-1-cyclohexenyl)-cyclohexanone was 38%.

Workup

  1. customdid not exceed 15° C.
  2. customthe product thus formed
  3. extractionwas extracted with ether
  4. washthe extract was washed with 1N hydrochloric acid and water in this turn
  5. distillationthe solvent was distilled off
  6. customAfter the residue was purified by column chromatography on silica gel (eluent: heptane/ethyl acetate=3/1)
  7. distillationthe solvent was distilled off
  8. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-3d7c736a0b5e4a0ebeeb2966588c7b1a
Source dataset
uspto-grants-2004_02
Patent number
US06685995B1

Reaction notes

Loading…