Water → 1-hydroxy-2,3-dihydro-1H-indene-4-carbonitrile

HRID 1646607Notes

Reaction equation

HRID 1646607 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][C:7]2=[O:12])#[N:2].[BH4-].[K+].O>O1CCCC1>[OH:12][CH:7]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:3]([C:1]#[N:2])[C:4]=2[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 27515831-Oxo-2,3-Dihydro-1H-Indene-4-CarbonitrileHCID 4192641Potassium borohydride

Product 1

HCID 145153071-hydroxy-2,3-dihydro-1H-indene-4-carbonitrileYield 94.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.46 g of 4-cyano-1-indanone in 131 ml of tetrahydrofuran is cooled to +5° C., 1 g of potassium borohydride is added in small fractions, with agitation for one hour 15 minutes, followed by pouring over 200 ml of water containing sodium chloride, and extraction with isopropyl ether. The organic phase is dried, brought to dryness under reduced pressure and the residue is chromatographed on silica in a hexane-ethyl acetate mixture (6-4). 1.40 g of expected product is obtained, M.p.=98° C.

Workup

  1. additioncontaining
  2. extractionsodium chloride, and extraction with isopropyl ether
  3. customThe organic phase is dried
  4. customthe residue is chromatographed on silica in a hexane-ethyl acetate mixture (6-4)

Sources & evidence

ORD record
ord-3d6a303bbf2a4ede8595cd26d21fe8b9
Source dataset
uspto-grants-1993_01
Patent number
US05180741

Reaction notes

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