Ethanol → HCID 22767863, compound

HRID 437833Notes

Reaction equation

HRID 437833 reaction equation
C[C:2]1[CH:19]=[CH:18][C:5]2[O:6][C:7]3[CH:15]=[CH:14][C:13]([S:16][CH3:17])=[CH:12][C:8]=3[C:9](=[O:11])[CH2:10][C:4]=2[CH:3]=1.[CH2:20](O)C.[BH4-].[Na+].O>CO>[CH3:20][C:19]1[CH:2]=[CH:3][C:4]2[CH2:10][CH:9]([OH:11])[C:8]3[CH:12]=[C:13]([S:16][CH3:17])[CH:14]=[CH:15][C:7]=3[O:6][C:5]=2[CH:18]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 22767910HCID 22767910, compound

Product 1

HCID 22767863HCID 22767863, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8.9 G. of 10,11-dihydro-2-methyl-8-methylthio-dibenz[b,f]oxepin-10-one are suspended in 65 ml. of ethanol and treated with a solution of 1.25 g. of sodium borohydride in 4.3 ml. of water. The mixture is stirred for 2 hours at room temperature. Then, 20 ml. of methanol are added thereto and the resulting mixture is heated at reflux for 15 minutes. Thereafter, the methanol and ethanol are removed by evaporation in vacuo. The residue is extracted with chloroform, the chloroform extracts are washed with water, dried and evaporated in vacuo. The residue is crystallized from diisopropyl ether, and there is obtained 10,11-dihydro- 3-methyl-8-methylthio-dibenz[b,f]oxepin- 10-ol having a melting point of 67°-69° C.

Workup

  1. temperaturethe resulting mixture is heated
  2. temperatureat reflux for 15 minutes
  3. customThereafter, the methanol and ethanol are removed by evaporation in vacuo
  4. extractionThe residue is extracted with chloroform
  5. washthe chloroform extracts are washed with water
  6. customdried
  7. customevaporated in vacuo
  8. customThe residue is crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-48dc95edeb00415cb1b2b4ccebdd4159
Source dataset
uspto-grants-1977_06
Patent number
US04032525

Reaction notes

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