Borane → 3-Hydroxymethyl-10,11-dihydro-11-oxodibenzo[b,f]-thiepin

HRID 1075017Notes

Reaction equation

HRID 1075017 reaction equation
[O:1]=[C:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[S:5][C:4]2[CH:13]=[C:14]([C:17](O)=[O:18])[CH:15]=[CH:16][C:3]1=2.B.C(OCC)(=O)C>O1CCCC1.O>[OH:18][CH2:17][C:14]1[CH:15]=[CH:16][C:3]2[C:2](=[O:1])[CH2:8][C:7]3[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=3[S:5][C:4]=2[CH:13]=1

Participants

6

Reactant 3

HCID 6331BoraneHCID 8857Ethyl AcetateHCID 8270515-oxo-6H-benzo[b][1]benzothiepine-2-carboxylic acid

Product 1

HCID 202702423-Hydroxymethyl-10,11-dihydro-11-oxodibenzo[b,f]-thiepin

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Dissolve 5.1 gm. of 10,11-dihydro-11-oxodibenzo[b,f]thiepin-3-carboxylic acid in 100 cc. of tetrahydrofuran and add 35 cc. of 1M borane in tetrahydrofuran at room temperature under a nitrogen atmosphere. Stir the mixture at room temperature for 3 hours. Slowly dilute the reaction mixture with water and then with ethyl acetate. Wash with aqueous sodium chloride, dry and evaporate to an oil.

Workup

  1. dissolutionDissolve 5.1 gm
  2. customat room temperature
  3. washWash with aqueous sodium chloride
  4. customdry
  5. customevaporate to an oil

Sources & evidence

ORD record
ord-bb68a86f61774eafb9c9a82a3f8f387b
Source dataset
uspto-grants-1983_07
Patent number
US04394515

Reaction notes

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