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

HRID 485421Notes

Reaction equation

HRID 485421 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-bd4a1abf95c9446891f8581486798769
Source dataset
uspto-grants-1985_08
Patent number
US04536507

Reaction notes

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