HCID 21459446, compound → HCID 21459437, compound
Reaction equation
[F:1][C:2]([F:29])([F:28])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH:12]2[CH2:17][CH2:16][CH:15]([CH:18]3[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25][CH:26]=[O:27])[CH2:20][CH2:19]3)[CH2:14][CH2:13]2)=[CH:6][CH:5]=1>C(O)C>[F:1][C:2]([F:28])([F:29])[O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][CH:12]2[CH2:13][CH2:14][CH:15]([CH:18]3[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25][CH2:26][OH:27])[CH2:20][CH2:19]3)[CH2:16][CH2:17]2)=[CH:8][CH:9]=1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Ethanol (20 ml) was added to the above 3-(4-(4-(2-(4-trifluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl) propanal (2.70 g, 6.58 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 liquid 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, distilling off the solvent, and recrystallizing the residue from heptane, to obtain 3-(4-(4-(2-(4-trifluoromethoxyphenyl)ethyl)cyclohexyl)cyclohexyl)propanol (2.10 g, 5.09 mmol). Yield: 77.4%.
Workup
- additionadding
- customexceed 10° C.
- extractionextracting the resulting product with ethyl acetate
- washwashing the organic layer successively with a saturated aqueous solution of sodium bicarbonate and water
- dry with materialdrying over magnesium sulfate
- distillationdistilling off the solvent
- customrecrystallizing the residue from heptane
Sources & evidence
- ORD record
- ord-029720e20d7844ab93b221302b2311c1
- Source dataset
- uspto-grants-1997_12
- Patent number
- US05702641
Reaction notes
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