Sodium borohydride → HCID 12374925, compound

HRID 1732775Notes

Reaction equation

HRID 1732775 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[C:5]([F:21])=[CH:6][C:7]2[S:13][C:12]3[CH:14]=[C:15]([F:18])[CH:16]=[CH:17][C:11]=3[CH2:10][C:9](=[O:19])[C:8]=2[CH:20]=1>O.[OH-].[Na+].O1CCOCC1>[Cl:3][C:4]1[C:5]([F:21])=[CH:6][C:7]2[S:13][C:12]3[CH:14]=[C:15]([F:18])[CH:16]=[CH:17][C:11]=3[CH2:10][CH:9]([OH:19])[C:8]=2[CH:20]=1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 12374921HCID 12374921, compound

Product 1

HCID 12374925HCID 12374925, compound

Reagents, catalysts & solvents 3

HCID 14798Sodium HydroxideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of sodium borohydride (1.0 g) in water (3 ml) containing 2 drops of 20% sodium hydroxide solution was added dropwise to a stirred solution of the ketone from the preceding experiment (7.9 g) in dioxane (100 ml). The mixture was refluxed for 6 hours, the dioxane evaporated in vacuo and the residue mixed with water and extracted with benzene. Evaporation of the extract and crystallization of the residue from an ether-cyclohexane mixture yielded 6.0 g of the pure 8-chloro-3,7-difluoro-10-hydroxy-10,11-dihydrodibenzo(b,f)thiepine, m.p. 84°-86° C.

Workup

  1. temperatureThe mixture was refluxed for 6 hours
  2. customthe dioxane evaporated in vacuo
  3. additionthe residue mixed with water
  4. extractionextracted with benzene
  5. customEvaporation of the
  6. extractionextract
  7. customcrystallization of the residue from an ether-cyclohexane mixture

Sources & evidence

ORD record
ord-7a0ffffab54c482da9d09a760021669e
Source dataset
uspto-grants-1980_12
Patent number
US04238611

Reaction notes

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