Sodium Hydroxide → HCID 12271957, compound

HRID 1732766Notes

Reaction equation

HRID 1732766 reaction equation
[BH4-].[Na+].[OH-].[Na+].[Cl:5][C:6]1[C:21]([F:22])=[CH:20][C:9]2[C:10](=[O:19])[CH2:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[S:14][C:8]=2[CH:7]=1>O.C(O)C.C1C=CC=CC=1>[Cl:5][C:6]1[C:21]([F:22])=[CH:20][C:9]2[CH:10]([OH:19])[CH2:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[S:14][C:8]=2[CH:7]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 12271952HCID 12271952, compound

Product 1

HCID 12271957HCID 12271957, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of sodium borohydride (0.42 g) in water (4 ml), containing 15% sodium hydroxide solution (0.1 ml), was added dropwise to a solution of the ketone from the preceding experiment (7.0 g) in a mixture of ethanol (70 ml) and benzene (25 ml). The mixture was refluxed for 3 hours, diluted with water and extracted with benzene. The extract was washed with 5% sodium hydroxide solution and water, dried over sodium sulphate and taken down. The solid residue was crystallized from hexane (30 ml), yielding 6.60 g (94%) of 7-chloro-8-fluoro-10-hydroxy-10,11-dihydrodibenzo(b,f)thiepine, m.p. 86°-87° C.

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. extractionextracted with benzene
  3. washThe extract was washed with 5% sodium hydroxide solution and water
  4. dry with materialdried over sodium sulphate
  5. customThe solid residue was crystallized from hexane (30 ml)

Sources & evidence

ORD record
ord-12424d9ad1ba4cf49a4238423eb9c0fe
Source dataset
uspto-grants-1980_12
Patent number
US04238611

Reaction notes

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