Ethanol → 8-Fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]-thiepin-10-ol

HRID 441987Notes

Reaction equation

HRID 441987 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=[CH:13][C:14]([CH3:16])=[CH:15][C:9]=3[CH2:8][C:7](=[O:17])[C:6]=2[CH:18]=1.C(O)C.[BH4-].[Na+]>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=[CH:13][C:14]([CH3:16])=[CH:15][C:9]=3[CH2:8][CH:7]([OH:17])[C:6]=2[CH:18]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 122755418-fluoro-2-methyl-dibenzo[b,f]thiepin-10(11H)-one

Product 1

HCID 122755428-Fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]-thiepin-10-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

103 G. of 8-fluoro-2-methyl-dibenzo[b,f]-thiepin-10(11H)-one is suspended in 550 ml. of ethanol and mixed with 24.3 g. of sodium borohydride. The reaction mixture is heated for about 10 minutes under reflux conditions. The reaction mixture, after the addition of water, is extracted with chloroform. The organic phase is again washed with water, dried over sodium sulfate and evaporated, whereby there is obtained 8-fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]-thiepin-10-ol as an oil.

Workup

  1. temperatureThe reaction mixture is heated for about 10 minutes under reflux conditions
  2. extractionis extracted with chloroform
  3. washThe organic phase is again washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-040311cdda7249b697f8c6b739b90347
Source dataset
uspto-grants-1977_08
Patent number
US04044010

Reaction notes

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