Methanol → 5-(trifluoromethyl)-2,3-dihydro-1H-inden-1-ol

HRID 2244907Notes

Reaction equation

HRID 2244907 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6]2.[BH4-].[Na+].CO>C1COCC1>[F:1][C:2]([F:13])([F:14])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH:8]([OH:12])[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 121749875-(Trifluoromethyl)indan-1-one

Product 1

HCID 248204735-(trifluoromethyl)-2,3-dihydro-1H-inden-1-olYield 107.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(trifluoromethyl)indan-1-one (0.7 g, 3 mmol) in THF (5 mL) cooled in an ice bath was added sodium borohydride (0.1 g, 3 mmol) followed by MeOH (1 mL). After being stirred for 30 min, the reaction was quenched with aqueous NaHCO3. The resulting solution was extracted with EtOAc twice. The extracts were washed with brine, dried (MgSO4), filtered and, concentrated. The crude material was purified by flash chromatography on silica eluting with 20% EtOAc/hexane to afford the desired product (0.65 g, 92%) as an oil. LC/MS calculated for C10H9F3O: (M+H)+ 203; found 185.1 (M+H—H2O)+.

Workup

  1. customthe reaction was quenched with aqueous NaHCO3
  2. extractionThe resulting solution was extracted with EtOAc twice
  3. washThe extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by flash chromatography on silica eluting with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-42a33bca6e93498eacb2edf6ccb39bb3
Source dataset
uspto-grants-2010_03
Patent number
US07678798B2

Reaction notes

Loading…