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

HRID 372165Notes

Reaction equation

HRID 372165 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 are suspended in 550 ml. of ethanol and treated with 24.3 g. of sodium borohydride. The mixture is heated under reflux for about 10 minutes. After the addition of water, the mixture is extracted with chloroform. The organic phase is washed with water, dried over sodium sulfate and evaporated, and there is obtained racemic 8-fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10ol as an oil.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for about 10 minutes
  3. extractionthe mixture is extracted with chloroform
  4. washThe organic phase is washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-43fff51f1c22490ca3eff841a0b31683
Source dataset
uspto-grants-1978_05
Patent number
US04089861

Reaction notes

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