Water → 6,11-Dihydrodibenzo[b,e]thiepin-11-ol
Reaction equation
[CH2:1]1[C:11]2[C:10](=[O:12])[C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[CH2:7][S:6][C:5]=2[CH:4]=[CH:3][CH2:2]1.[BH4-].[Na+].O>CO>[CH:1]1[C:11]2[CH:10]([OH:12])[C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[CH2:7][S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
48 g (212 mmol) 6.1-dihydro-dibenzo[b,e]thiepin-11-one are dissolved in 480 ml absolute methanol and cooled to ca. −10° C. 19.2 g (507 mmol) sodium borohydride is added portion wise to this solution. The mixture is stirred for three hours at RT without further cooling. After the careful addition of 30 ml water, the suspension is concentrated under vacuum. The residue is taken up in 500 ml dichloromethane and washed twice each with 150 ml water. The organic phase is dried over sodium sulfate and the solvent is removed under vacuum. The residue is crystallized from 180 ml toluene. Colorless crystals of MP. 108° C.: Yield 41.2 g (85%).
Workup
- concentrationthe suspension is concentrated under vacuum
- washwashed twice each with 150 ml water
- dry with materialThe organic phase is dried over sodium sulfate
- customthe solvent is removed under vacuum
- customThe residue is crystallized from 180 ml toluene
- customColorless crystals of MP. 108° C.
Sources & evidence
- ORD record
- ord-fbb0fcc1a2a4403ea336f5b67dca685a
- Source dataset
- uspto-grants-2005_06
- Patent number
- US06903118B1
Reaction notes
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