Sodium borohydride → HCID 53845926, compound

HRID 1742419Notes

Reaction equation

HRID 1742419 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:12](=[O:14])[CH3:13])=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[BH4-].[Na+]>CO>[OH:1][CH:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:12](=[O:14])[CH3:13])=[CH:8][CH:9]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22755584HCID 22755584, compound

Product 1

HCID 53845926HCID 53845926, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of acetic acid 1-oxo-indan-5-yl ester (2700 mg, 14.2 mmol) in MeOH (20 mL) at 0° C. was added sodium borohydride (760 mg, 20 mmol). The reaction mixture was stirred for 2 hours, quenched with saturated aqueous NH4Cl (20 mL) and diluted with ethyl acetate (500 mL). The organic solution was washed with saturated aqueous NaHCO3 (50 mL) and saturated aqueous NaCl (50 mL), dried (Na2SO4) and concentrated in vacuo to give 2.3 grams of the desired product. 1H NMR (250 MHz, CDCl3): d 7.35 (d, 2 H), 6.90 (m, 2 H), 5.2 (t, 1 H), 3.0 (m, 1 H), 2.8 (m, 1 H), 2.5 (m, 1 H), 2.3 (s, 3 H), 1.95 (1 H, m).

Workup

  1. customquenched with saturated aqueous NH4Cl (20 mL)
  2. additiondiluted with ethyl acetate (500 mL)
  3. washThe organic solution was washed with saturated aqueous NaHCO3 (50 mL) and saturated aqueous NaCl (50 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a782773c85e04e8bb3bce2113b80cf34
Source dataset
uspto-grants-1994_08
Patent number
US05338740

Reaction notes

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