1-Oxo-2,3-Dihydro-1H-Indene-4-Carbonitrile → 1-hydroxy-2,3-dihydro-1H-indene-4-carbonitrile

HRID 1809490Notes

Reaction equation

HRID 1809490 reaction equation
[O:1]=[C:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]#[N:12])[C:5]=2[CH2:4][CH2:3]1.[BH4-].[Na+]>CCO>[OH:1][CH:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]#[N:12])[C:5]=2[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 27515831-Oxo-2,3-Dihydro-1H-Indene-4-CarbonitrileHCID 4311764Sodium borohydride

Product 1

HCID 145153071-hydroxy-2,3-dihydro-1H-indene-4-carbonitrileYield 83.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred suspension of 1-oxo-2,3-dihydro-1H-indene-4-carbonitrile (1.2 g, 7.64 mmol) and silica gel (catalytic) in EtOH at 0° C. was added NaBH4 (237.2 mg, 7.64 mmol). The reaction was allowed to warm to room temperature and stirred for 2 h. The solvent was removed under reduced pressure, and the product was purified by chromatography (50% EA/hexane) to afford 1.02 g (82.3%) of 1-hydroxy-2,3-dihydro-1H-indene-4-carbonitrile as white solid. LCMS-ESI (m/z) calculated for C10H9NO; 159.18; found 160.1 [M+H]+, tR=2.39 min.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe product was purified by chromatography (50% EA/hexane)

Sources & evidence

ORD record
ord-6bad1a5e647248dba2b4c180c57ffafc
Source dataset
uspto-grants-2013_01
Patent number
US08362048B2

Reaction notes

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