Methanol → 6-(Trifluoromethyl)-2,3-dihydro-1H-inden-1-OL

HRID 2178756Notes

Reaction equation

HRID 2178756 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][C:9]2=[O:12])=[CH:5][CH:4]=1.[BH4-].[Na+].CO>C1COCC1>[F:1][C:2]([F:13])([F:14])[C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[OH:12])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 227541286-(Trifluoromethyl)-1-indanone

Product 1

HCID 592126636-(Trifluoromethyl)-2,3-dihydro-1H-inden-1-OLYield 68.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(trifluoromethyl)indan-1-one (2.20 g, 11 mmol) in THF (30 mL) was added sodium borohydride (0.50 g, 13 mmol). After being stirred for 30 min, methanol (10 mL) was added slowly. Stirring was continued for 2 hrs. The reaction was quenched by addition of an aqueous ammonium chloride solution. The two layers were separated and the water layer was extracted by ether. The combined organic layers were washed with water, brine, dried over MgSO4 and concentrated. Column chromatography on silica (10-15% EtOAC in hexane) gave the title compound (1.52 g, 68%) as an oil. MS calculated for C10H9F3O: (M+H)+203; found 185.0 (M−H2O+1)+.

Workup

  1. stirringStirring
  2. waitwas continued for 2 hrs
  3. customThe reaction was quenched by addition of an aqueous ammonium chloride solution
  4. customThe two layers were separated
  5. extractionthe water layer was extracted by ether
  6. washThe combined organic layers were washed with water, brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-07d571165f544b98b46ea7b001d78e1e
Source dataset
uspto-grants-2015_06
Patent number
US09067921B2

Reaction notes

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