HCID 21459472, compound → HCID 21459451, compound

HRID 1941037Notes

Reaction equation

HRID 1941037 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH:11]2[CH2:16][CH2:15][CH:14]([CH:17]3[CH2:22][CH2:21][CH:20]([CH2:23][CH2:24][CH:25]=[O:26])[CH2:19][CH2:18]3)[CH2:13][CH2:12]2)=[CH:5][CH:4]=1>C(O)C>[F:1][C:2]([F:27])([F:28])[C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][CH:11]2[CH2:12][CH2:13][CH:14]([CH:17]3[CH2:22][CH2:21][CH:20]([CH2:23][CH2:24][CH2:25][OH:26])[CH2:19][CH2:18]3)[CH2:15][CH2:16]2)=[CH:7][CH:8]=1

Participants

3

Reactant 1

HCID 21459472HCID 21459472, compound

Product 1

HCID 21459451HCID 21459451, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Ethanol (10 ml) was added to the above 3-(4-(4-(2-(4-trifluoromethylphenyl)ethyl)cyclohexyl)cyclohexyl)propanal (1.21 g, 3.07 mmol), followed by cooling the mixture down to 0° C. in a nitrogen gas atmosphere, adding thereto, sodiumboronhydride (0.13 g, 3.43 mmol) so that the solution temperature could not exceed 10° C., stirring the mixture at 0° C. for 2 hours, extracting the resulting product with ethyl acetate, washing the organic layer successively with a saturated, aqueous solution of sodium bicarbonate and water, drying over magnesium sulfate, and distilling off the solvent, to obtain 3-(4-(4-(2-(4-trifluoromethylphenyl)ethyl)cyclohexyl)cyclohexyl)propanol (1.20 g, 3.03 mmol). The yield was 98.7%.

Workup

  1. additionadding
  2. customexceed 10° C.
  3. extractionextracting the resulting product with ethyl acetate
  4. washwashing the organic layer successively with a saturated, aqueous solution of sodium bicarbonate and water
  5. dry with materialdrying over magnesium sulfate
  6. distillationdistilling off the solvent

Sources & evidence

ORD record
ord-85019b381ba0426c8a6c9f7c744ba707
Source dataset
uspto-grants-1997_12
Patent number
US05702641

Reaction notes

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