1-Indanone, 6-bromo- → 6-bromo-2,3-dihydro-1H-inden-1-ol

HRID 896068Notes

Reaction equation

HRID 896068 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[OH:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1397781-Indanone, 6-bromo-HCID 4311764Sodium borohydride

Product 1

HCID 27548246-bromo-2,3-dihydro-1H-inden-1-olYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-bromo-1-indanone (prepared as described by Cornelius, Lyndon A. M. and Combs, Donald W. Synth. Commun. (1994), 24(19), 2777-88) (1.4 g, 6.57 mmol) in 20 mL of methanol was added sodium borohydride (0.087 g, 2.3 mmol) over a period of five minutes at room temperature. The reaction mixture was stirred for two hours at room temperature, concentrated under pressure and partitioned between ethyl acetate (50 mL) and 1N HCl (20 mL). The ethyl acetate layer was dried over sodium sulfate and concentrated under reduced pressure to yield the title compound as a solid (1.4 g, 99%). 1H NMR (CDCl3): δ 7.45 (s, 1H), 7.3 (d, 1H), 7.0 (d, 1H), 5.2 (t, 1H), 2.9 (m, 1H), 2.7 (m, 1H), 2.4 (m, 1H), 1.9 (m, 2H).

Workup

  1. concentrationconcentrated under pressure
  2. custompartitioned between ethyl acetate (50 mL) and 1N HCl (20 mL)
  3. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e2d1d48b2e634a9784938743713600a1
Source dataset
uspto-grants-2005_07
Patent number
US06919335B2

Reaction notes

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