Hydrochloric Acid → HCID 86657643, compound

HRID 217448Notes

Reaction equation

HRID 217448 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][C@@H:13]([CH3:18])[C:14]([F:17])([F:16])[F:15])[C:6](O)=[O:7].B.C1COCC1.Cl>C1COCC1>[F:1][C:2]([F:19])([F:20])[C:3]1[CH:4]=[C:5]([CH2:6][OH:7])[CH:9]=[CH:10][C:11]=1[O:12][C@@H:13]([CH3:18])[C:14]([F:15])([F:16])[F:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 59214330HCID 59214330, compound

Product 1

HCID 86657643HCID 86657643, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-(trifluoromethyl)-4-[(1S)-2,2,2-trifluoro-1-methylethoxy]benzoic acid (1.085 g) in THF (43 mL) was added dropwise a solution of BH3.THF in THF (1 M, 14 mL) at 0° C. The reaction mixture was warmed to room temperature and then stirred for 15 hours. To the reaction liquid was added 1 M hydrochloric acid at 0° C. to stop the reaction, followed by stirring for 30 minutes and extracting with EtOAc. The organic layer was washed with brine, dried over MgSO4, and then concentrated under reduced pressure to obtain {3-(trifluoromethyl)-4-[(1S)-2,2,2-trifluoro-1-methylethoxy]phenyl}methanol (570 mg) as a white oily substance.

Workup

  1. customTo the reaction liquid
  2. customthe reaction
  3. stirringby stirring for 30 minutes
  4. extractionextracting with EtOAc
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3c4e0733d98d457d8e2499e7223492f3
Source dataset
uspto-grants-2012_06
Patent number
US08193378B2

Reaction notes

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