Water → 10,11-Dihydro-2-trifluoromethyl-dibenzo[b,f]thiepin-10-ol

HRID 435658Notes

Reaction equation

[F:1][C:2]([F:20])([F:19])[C:3]1[CH:18]=[CH:17][C:6]2[S:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[C:10](=[O:12])[CH2:11][C:5]=2[CH:4]=1.[BH4-].[Na+].O.C(Cl)(Cl)Cl>C(O)C>[F:20][C:2]([F:1])([F:19])[C:3]1[CH:18]=[CH:17][C:6]2[S:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[CH:10]([OH:12])[CH2:11][C:5]=2[CH:4]=1

Participants

Conditions

Temperature: 30 °C

Procedure

12 g of 10,11-dihydro-2-trifluoromethyl-dibenzo[b,f]-thiepin-10-one are dissolved in 110 ml of absolute ethanol and treated with 4 g of sodium borohydride. The mixture is held at reflux for 12 minutes, cooled to 30° C and treated with 350 ml of water and 100 ml of chloroform. After equilibration, the organic phase is washed with aqueous sodium chloride solution, dried over sodium sulphate and evaporated under reduced pressure. There is obtained 10,11-dihydro-2-trifluoromethyl-dibenzo[b,f]thiepin-10-ol in the form of yellow crystals which melt at 122°-123° C.

Workup

temperatureat reflux for 12 minutes
washAfter equilibration, the organic phase is washed with aqueous sodium chloride solution
dry with materialdried over sodium sulphate
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-b580036d12424d9a9647f84b78065018
Source dataset: uspto-grants-1977_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04006145

Reaction notes

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