Ethanol → 10,11-Dihydro-3-methoxy-8-(methylthio)-dibenzo thiepin-10-ol

HRID 1075873Notes

Reaction equation

HRID 1075873 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][C:11](=O)[C:10]3[CH:14]=[C:15]([S:18][CH3:19])[CH:16]=[CH:17][C:9]=3[S:8][C:7]=2[CH:20]=1.C([OH:23])C.[BH4-].[Na+]>O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:12]3[CH2:11][CH:10]([OH:23])[CH:14]=[C:15]([S:18][CH3:19])[C:16]=3[CH:17]=[CH:9][S:8][C:7]=2[CH:20]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 128221953-methoxy-8-methylthio-dibenzo[b,f]thiepin-10(11H)-one

Product 1

HCID 2154119710,11-Dihydro-3-methoxy-8-(methylthio)-dibenzo thiepin-10-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

17.8 G. of 3-methoxy-8-(methylthio)-dibenzo[b,f]thiepin-10(11H)-one is suspended in 150 ml. of ethanol and reacted with 38 g. of sodium borohydride. The reaction mixture is stirred for 90 minutes, and subsequently treated with water and extracted with ether. The organic phase is washed with water, dried over magnesium sulfate and evaporated, whereby there is obtained 10,11-dihydro-3-methoxy-8-(methylthio)-dibenzo[d,f]thiepin-10-ol having a melting point of 122°-124°.

Workup

  1. extractionextracted with ether
  2. washThe organic phase is washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-bee840270add48898f1237dbb4de0ce9
Source dataset
uspto-grants-1976_05
Patent number
US03954764

Reaction notes

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