5-oxo-6H-benzo[b][1]benzothiepine-2-carboxylic acid → 10,11-Dihydro-11-hydroxydibenzo[b,f]thiepin-3-carboxylic Acid

HRID 1074984Notes

Reaction equation

HRID 1074984 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]([OH:19])=[O:18])[CH:15]=[CH:16][C:3]1=2.[BH4-].[Na+]>C(=O)(O)[O-].[Na+]>[OH:1][CH: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]([OH:19])=[O:18])[CH:15]=[CH:16][C:3]1=2

Participants

4

Reactant 2

HCID 8270515-oxo-6H-benzo[b][1]benzothiepine-2-carboxylic acidHCID 4311764Sodium borohydride

Product 1

HCID 1315185610,11-Dihydro-11-hydroxydibenzo[b,f]thiepin-3-carboxylic AcidYield 96.2%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

16.3 G. 10,11-dihydro-11-oxodibenzo[b,f]thiepin-3-carboxylic acid is stirred in aqueous sodium bicarbonate solution and 5 g. sodium borohydride is added in portions. The foaming mixture is stirred for an additional half hour. The solution is extracted with ether and the aqueous layer acidified with hydrochloric acid and the solid filtered and dried to yield 15.8 g. of the desired yellow solid (96.2% yield), m.p. 202°-204° C.

Workup

  1. extractionThe solution is extracted with ether
  2. filtrationthe solid filtered
  3. customdried
  4. customto yield 15.8 g

Sources & evidence

ORD record
ord-8ed379cb4eed4b76837c732f5e9b103e
Source dataset
uspto-grants-1983_07
Patent number
US04394515

Reaction notes

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