Hydrochloric Acid → HCID 178520944, compound

HRID 2172243Notes

Reaction equation

HRID 2172243 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.Cl>O1CCCC1>[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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178525709HCID 178525709, compound

Product 1

HCID 178520944HCID 178520944, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

cis-4-(Trifluoromethyl)cyclohexanecarboxylic acid (1.05 g, 5.4 mmol) and tetrahydrofuran (20 ml) were mixed and ice-cooled. A borane-tetrahydrofuran complex (10.71 ml, 10.7 mmol) was added to the mixture dropwise. After the completion of dropwise addition, the reaction mixture was stirred at room temperature overnight. 1 N hydrochloric acid was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution, dried over sodium sulfate, and concentrated to afford the title compound as a colorless oil (0.92 g, 94%).

Workup

  1. temperatureice-cooled
  2. additionA borane-tetrahydrofuran complex (10.71 ml, 10.7 mmol) was added to the mixture dropwise
  3. additionAfter the completion of dropwise addition
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materiala saturated sodium chloride aqueous solution, dried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7540266f46bb4a14b916614f67707c98
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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