HCID 178525710, compound → HCID 178520945, compound

HRID 81259Notes

Reaction equation

HRID 81259 reaction equation
[F:1][C:2]([F:13])([F:12])[C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9](O)=[O:10])[CH2:5][CH2:4]1>C1COCC1>[F:1][C:2]([F:12])([F:13])[C@H:3]1[CH2:4][CH2:5][C@H:6]([CH2:9][OH:10])[CH2:7][CH2:8]1

Participants

3

Reactant 1

HCID 178525710HCID 178525710, compound

Product 1

HCID 178520945HCID 178520945, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

BH3 (100 mL, 0.1 mol, 1.0 M solution in THF) was added dropwise to 0° C. solution of trans-4-(trifluoromethyl)cyclohexanecarboxylic acid (19.6 g, 0.1 mol) in dry THF (100 mL). The reaction was stirred at room temperature for 5 h, quenched with water, extracted with EtOAc, washed with brine, dried over Na2SO4, filtered, and concentrated to give [trans-4-(trifluoromethyl)cyclohexyl]methanol. 1H NMR (300 MHz, CDCl3): δ 3.48-3.47 (d, 2H), 2.00-1.89 (m, 5H), 1.51-1.43 (m, 1H), 1.35-1.26 (m, 2H), 1.05-0.96 (m, 2H).

Workup

  1. customquenched with water
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5f33ae438b93447eacece0ab20229db9
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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