Sodium borohydride → 4-(4-(2-(4-n-Pentyl-cyclohexyl)ethyl)-3-cyclohexenyl)cyclohexanol

HRID 2119284Notes

Reaction equation

HRID 2119284 reaction equation
C(O)C.C1COCC1.[CH2:9]([CH:14]1[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][C:22]2[CH2:27][CH2:26][CH:25]([CH:28]3[CH2:33][CH2:32][C:31](=[O:34])[CH2:30][CH2:29]3)[CH2:24][CH:23]=2)[CH2:16][CH2:15]1)[CH2:10][CH2:11][CH2:12][CH3:13].[BH4-].[Na+]>O>[CH2:9]([CH:14]1[CH2:15][CH2:16][CH:17]([CH2:20][CH2:21][C:22]2[CH2:27][CH2:26][CH:25]([CH:28]3[CH2:33][CH2:32][CH:31]([OH:34])[CH2:30][CH2:29]3)[CH2:24][CH:23]=2)[CH2:18][CH2:19]1)[CH2:10][CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 21873804Tetrahydrofuran ethanolHCID 234403814-(4-(2-(4-n-Pentylcyclohexyl)ethyl)-3-cyclohexenyl)cyclohexanone

Product 1

HCID 234403854-(4-(2-(4-n-Pentyl-cyclohexyl)ethyl)-3-cyclohexenyl)cyclohexanolYield 40.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To 1 l of mixed solvent of ethanol/THF (4/1) was dissolved 15.0 g (41.8 mmol) of the 4-(4-(2-(4-n-pentylcyclohexyl)ethyl)-3-cyclohexenyl)cyclohexanone described above, and the solution was cooled down to 0° C. To this mixture was gradually added 0.80 g (21.1 mmol) of sodium borohydride such that the liquid temperature did not exceed 15° C., and the mixture was stirred for 1 hour. Water in an amount of 350 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 6.0 g (17 mmol) of 4-(4-(2-(4-n-pentyl-cyclohexyl)ethyl)-3-cyclohexenyl)cyclohexanol. Yield of this compound based on 4-(4-(2-(4-n-pentylcyclohexyl)ethyl)-3-cyclohexenyl)cyclohexanone was 41%.

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-5214e6aae8e24c93a696e24ecef1cfa8
Source dataset
uspto-grants-2004_02
Patent number
US06685995B1

Reaction notes

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