Ethanol → 10,11-Dihydro-3-methoxy-8-methylthio-dibenzo[b,f]thiepin-10-ol

HRID 441989Notes

Reaction equation

HRID 441989 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][C:11](=[O:13])[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(O)C.[BH4-].[Na+]>O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH:11]([OH:13])[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

Participants

5

Reactant 3

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

Product 1

HCID 1282219810,11-Dihydro-3-methoxy-8-methylthio-dibenzo[b,f]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-dihydro3-methoxy-8-(methylthio)-dibenzo[b,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-4f8c4c43e2574d0094a84770c71cd5c1
Source dataset
uspto-grants-1977_08
Patent number
US04044010

Reaction notes

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