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

HRID 1973096Notes

Reaction equation

HRID 1973096 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, evaporated, and there is obtained 8-fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-ol 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-fe1b10b4f2be4ef197af9830db075d9b
Source dataset
uspto-grants-1976_12
Patent number
US03996229

Reaction notes

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