Sodium borohydride → 2-(1-Hydroxy-indan-5-yl)-benzonitrile

HRID 1742404Notes

Reaction equation

HRID 1742404 reaction equation
[BH4-].[Na+].[O:3]=[C:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]3[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=3[C:15]#[N:16])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1>CO>[OH:3][CH:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]3[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=3[C:15]#[N:16])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 190089072-(1-Oxo-indan-5-yl)-benzonitrile

Product 1

HCID 190089042-(1-Hydroxy-indan-5-yl)-benzonitrileYield 90.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (1.03 grams, 27 mmol) was added to a mixture of 2-(1-oxo-indan-5-yl)-benzonitrile (3.2 grams, 13.6 mmol) in methanol (MeOH) (130 mL) at ) 0° C. The reaction mixture was allowed to warm to room temperature and was stirred for 3 hours. After cooling to 0° C., the reaction mixture was quenched with saturated aqueous ammonium chloride (NH4Cl) (25 mL). EtOAc (500 mL) was added and the organic layer was separated and washed with saturated aqueous NaCl (3×100 mL), dried (Na2SO4) and concentrated in vacuo to yield 2.9 grams of a brown oil. 1H NMR (250 MHz, CDCl3): d 7.78 (d, 1 H), 7.65 (t, 1 H), 7.50 (m, 5 H), 5.32 (t, 1 H), 3.15 (m, 1 H), 2.92 (m, 1 H), 2.55 (m, 1 H), 2.0 (m, 1 H).

Workup

  1. temperatureAfter cooling to 0° C.
  2. customthe reaction mixture was quenched with saturated aqueous ammonium chloride (NH4Cl) (25 mL)
  3. additionEtOAc (500 mL) was added
  4. customthe organic layer was separated
  5. washwashed with saturated aqueous NaCl (3×100 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c623c803a20b4a9ca7bf714c5b961b68
Source dataset
uspto-grants-1994_08
Patent number
US05338740

Reaction notes

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