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

HRID 2402174Notes

Reaction equation

HRID 2402174 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+]>C(O)C>[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 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred suspension of 1-oxo-2,3-dihydro-1H-indene-4-carbonitrile (1.0 equiv, 0.4M) and silica gel (catalytic) in ethanol at 0° C. was added NaBH4 (⅓ equiv). The reaction was allowed to warm up to room temperature and stirred for 2 h. The Solvent was removed under reduced pressure and the product purified by CC in hexane/EtOAc (5:5) to offer 1-hydroxy-2,3-dihydro-1H-indene-4-carbonitrile in 80% yield.

Workup

  1. customThe Solvent was removed under reduced pressure
  2. customthe product purified by CC in hexane/EtOAc (5:5)

Sources & evidence

ORD record
ord-cd019026acc24190aeecd7a75bad701a
Source dataset
uspto-grants-2014_08
Patent number
US08796318B2

Reaction notes

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