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

HRID 1973103Notes

Reaction equation

HRID 1973103 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 are suspended in 150 ml. of ethanol and treated with 3.8 g. of sodium borohydride. The mixture is stirred for 90 minutes. Then, it is treated with water and extracted with ether. The organic phase is washed with water, dried over magnesium sulfate, evaporated, and there is obtained 10,11-dihydro-3-methoxy-8-methylthio-dibenzo[b,f]thiepin-10-ol having a melting point of 122°-124° C.

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-c1dec78aba7e49dda5666e2b32b88a19
Source dataset
uspto-grants-1976_12
Patent number
US03996229

Reaction notes

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