Ethanol → HCID 22767863, compound

HRID 866624Notes

Reaction equation

HRID 866624 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-9ff207ab064e429ea8285975f4193b7c
Source dataset
uspto-grants-1978_07
Patent number
US04100173

Reaction notes

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