HCID 21459434, compound → HCID 21459447, compound

HRID 1941046Notes

Reaction equation

HRID 1941046 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:13][CH2:14][CH:15]2[CH2:20][CH2:19][CH:18]([CH2:21][CH2:22][CH:23]=[O:24])[CH2:17][CH2:16]2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:12])([F:11])[F:10].B.[Na]>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH2:13][CH2:14][CH:15]2[CH2:20][CH2:19][CH:18]([CH2:21][CH2:22][CH2:23][OH:24])[CH2:17][CH2:16]2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:11])([F:12])[F:10]

Participants

4

Reactant 2

HCID 21459434HCID 21459434, compoundHCID 178418435HCID 178418435, compound

Product 1

HCID 21459447HCID 21459447, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Ethanol (12 ml) was added to the above 3-(4-(2-(3-fluoro-4-trifluoromethoxyphenyl)ethyl)cyclohexyl)propanal (1.76 g, 5.1 mmol), followed by cooling the mixture down to 0° C. in a nitrogen gas atmosphere, adding to the mixture, sodiumboron hydride (0.19 g, 5.0 mmol) so that the liquid temperature might 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 MgSO4, distilling off the solvent, and recrystallizing the residue with heptane, to obtain 3-(4-(2-(3-fluoro-4-trifluoromethoxyphenyl)ethyl)cyclohexyl)propanol (1.52 g, 4.4 mmol). Yield: 86.3%.

Workup

  1. customexceed 10° C.
  2. extractionextracting the resulting product with ethyl acetate
  3. washwashing the organic layer successively with a saturated, aqueous solution of sodium bicarbonate and water
  4. dry with materialdrying over MgSO4
  5. distillationdistilling off the solvent
  6. customrecrystallizing the residue with heptane

Sources & evidence

ORD record
ord-f10d479088be4413a96959267bba1a95
Source dataset
uspto-grants-1997_12
Patent number
US05702641

Reaction notes

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