Sodium borohydride → 5,6-Dichloro-2,3-dihydro-1H-inden-1-OL

HRID 2226532Notes

Reaction equation

HRID 2226532 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[Cl:13])[C:9](=[O:14])[CH2:8][CH2:7]2>CO>[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[Cl:13])[CH:9]([OH:14])[CH2:8][CH2:7]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 229036095,6-Dichloro-2,3-dihydro-1H-inden-1-one

Product 1

HCID 199195245,6-Dichloro-2,3-dihydro-1H-inden-1-OL

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4.85 g of sodium borohydride were added at 0° C. to a solution of 4 g of the product of Step A in 285 ml of methanol and after stirring for one hour, the methanol was evaporated. The residue was diluted with water and excess hydride was eliminated by addition of hydrochloric acid. The mixture was extracted with ethyl acetate and the organic phase was evaporated to dryness under reduced pressure to obtain the desired product melting at 84° C.

Workup

  1. customthe methanol was evaporated
  2. additionThe residue was diluted with water and excess hydride
  3. additionwas eliminated by addition of hydrochloric acid
  4. extractionThe mixture was extracted with ethyl acetate
  5. customthe organic phase was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-51a7bcfd90984e5e8c2b2e09bbbfcc4b
Source dataset
uspto-grants-1994_09
Patent number
US05348971

Reaction notes

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