Sodium Hydroxide → HCID 12374620, compound

HRID 1732773Notes

Reaction equation

HRID 1732773 reaction equation
[BH4-].[Na+].[OH-].[Na+].[Cl:5][C:6]1[C:7]([O:22][CH3:23])=[CH:8][C:9]2[S:15][C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[CH2:12][C:11](=[O:20])[C:10]=2[CH:21]=1>O.C1C=CC=CC=1.C(O)C>[Cl:5][C:6]1[C:7]([O:22][CH3:23])=[CH:8][C:9]2[S:15][C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[CH2:12][CH:11]([OH:20])[C:10]=2[CH:21]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 826393HCID 826393, compoundHCID 4311764Sodium borohydride

Product 1

HCID 12374620HCID 12374620, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium borohydride (0.5 g) in water (3.5 ml), containing 0.1 ml of 15% sodium hydroxide solution was slowly added dropwise to a solution of the ketone from the preceding preparation (6.2 g) in a mixture of benzene (40 ml) and ethanol (100 ml). The stirred mixture was refluxed for 3 hours, the volatile components evaporated under diminished pressure, the residue diluted with water and extracted with benzene. A conventional isolation procedure, followed by crystallization of the crude product from ethanol (25 ml), yielding 5.2 g (83%) of 8-chloro-10-hydroxy-7-methoxy-10,11-dihydrodibenzo(b,f)thiepine, m.p. 130°-132° C.

Workup

  1. temperatureThe stirred mixture was refluxed for 3 hours
  2. customthe volatile components evaporated under diminished pressure
  3. additionthe residue diluted with water
  4. extractionextracted with benzene
  5. customA conventional isolation procedure, followed by crystallization of the crude product from ethanol (25 ml)

Sources & evidence

ORD record
ord-b813ab279e35446f91c1fc849bfaffaa
Source dataset
uspto-grants-1980_12
Patent number
US04238611

Reaction notes

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