Water → HCID 11791018, compound

HRID 477779Notes

Reaction equation

HRID 477779 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[CH2:8][O:7][C:6]=2[CH:17]=1.[BH4-].[Na+].O>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:11]([OH:12])[C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[CH2:8][O:7][C:6]=2[CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 110751573-fluorodibenzo[b,e]oxepin-11(6H)-one

Product 1

HCID 11791018HCID 11791018, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2.0 g of 3-fluoro-6,11-dihydrodibenz[b,e]oxepin-11-one in 20 ml of methanol is added 0.5 g of sodium borohydride with ice-cooling and then the mixture is stirred at the same temperature for 1 hour. The reaction mixture is poured into water and the resultant is extracted with toluene. The extract is washed with water and then dried over magnesium sulfate. Toluene is distilled off to give 1.9 g of 3-fluoro-6,11-dihydrodibenz[b,e]oxepin-11-ol (crystals). Mass spectrum m/z: 230(M+).

Workup

  1. temperaturecooling
  2. extractionthe resultant is extracted with toluene
  3. washThe extract is washed with water
  4. dry with materialdried over magnesium sulfate
  5. distillationToluene is distilled off

Sources & evidence

ORD record
ord-bbee9ad46f224e4590e569f45ad15f0e
Source dataset
uspto-grants-1989_12
Patent number
US04889858

Reaction notes

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