Sodium → 6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-ol

HRID 1051106Notes

Reaction equation

HRID 1051106 reaction equation
[Na].[F:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:17]=[C:16]3[C:12]([CH2:13][CH2:14][C:15]3=[O:18])=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1>CO>[F:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:17]=[C:16]3[C:12]([CH2:13][CH2:14][CH:15]3[OH:18])=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 5360545SodiumHCID 820809706-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-one

Product 1

HCID 1181615566-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-olYield 100.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohyride (19 mg, 0.5 mmol) was added to a solution of 6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-one (55 mg, 0.24 mmol) and methanol (12 mL) in a 100 mL round bottom flask at 0° C. After stirring for 1 hour, the resulting mixture was warmed to room temperature. The reaction was quenched with saturated aqueous ammonium chloride (100 mL) and extracted with ethyl acetate (100 mL). The organic extract was dried (Na2SO4), filtered and concentrated. The resulting crude residue was purified by combiflash (4 g column, hexanes→100% ethyl acetate/hexanes, gradient) to afford 55 mg (99%) of 6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-ol.

Workup

  1. customThe reaction was quenched with saturated aqueous ammonium chloride (100 mL)
  2. extractionextracted with ethyl acetate (100 mL)
  3. extractionThe organic extract
  4. dry with materialwas dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting crude residue was purified by combiflash (4 g column, hexanes→100% ethyl acetate/hexanes, gradient)

Sources & evidence

ORD record
ord-89bd424ddfe34924b06aeea7b1c7bec7
Source dataset
uspto-grants-2016_07
Patent number
US09388153B2

Reaction notes

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