Sodium borohydride → HCID 19699318, compound

HRID 1735866Notes

Reaction equation

HRID 1735866 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[C:7](=[O:12])[CH2:6][CH2:5]2.[BH4-].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[CH:7]([OH:12])[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 117689445,6-Difluoro-1-indanone

Product 1

HCID 19699318HCID 19699318, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5,6-Difluoroindan-1-one (59.3 g, 0.353 mol) was dissolved in 1 L of ethanol and sodium borohydride (6.68 g, 0.176 mol) was added. The mixture was stirred for 48 hours and the ethanol was removed by evaporation under reduced pressure. The residue was partitioned between diethyl ether and water and the mixture was acidified with 1N hydrochloric acid. The mixture was dried over magnesium sulfate and filtered. The solvents were evaporated giving 5,6-difluoro-1-hydroxyindane (59.8 g) as an oil.

Workup

  1. customthe ethanol was removed by evaporation under reduced pressure
  2. customThe residue was partitioned between diethyl ether and water
  3. dry with materialThe mixture was dried over magnesium sulfate
  4. filtrationfiltered
  5. customThe solvents were evaporated

Sources & evidence

ORD record
ord-d50c262ba03040d5b14ad2b0f408479b
Source dataset
uspto-grants-1996_07
Patent number
US05538988

Reaction notes

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