Sodium Hydroxide → HCID 12756964, compound

HRID 1389284Notes

Reaction equation

HRID 1389284 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][C:10](=[O:12])[C:9]3[CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=[CH:16][C:8]=3[S:7][C:6]=2[CH:20]=1.[BH4-].[Na+].[OH-].[Na+]>O1CCOCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH:10]([OH:12])[C:9]3[CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=[CH:16][C:8]=3[S:7][C:6]=2[CH:20]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 12756957HCID 12756957, compound

Product 1

HCID 12756964HCID 12756964, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 6.9 g of the foregoing ketone in 90 ml of dioxane was treated dropwise with a solution of 9.8 g of sodium borohydride in 3 ml of water containing 1 drop of a 20% sodium hydroxide solution. The mixture was stirred for 2 hours at room temperature and after standing overnight, dioxane evaporated. The residue was diluted with water, acidified with hydrochloric acid and the product extracted with chloroform. Processing of the extract and crystallization of the crude product from benzene yielded 4.1 g pure 3-fluoro-8-nitro-10,11-dihydrodibenzo(b,f)thiepin-10-ol, m.p. 133°-135° C.

Workup

  1. waitafter standing overnight
  2. customdioxane evaporated
  3. additionThe residue was diluted with water
  4. extractionthe product extracted with chloroform
  5. extractionProcessing of the extract
  6. customcrystallization of the crude product from benzene

Sources & evidence

ORD record
ord-d7476533aae449e898075179b0b1c1b7
Source dataset
uspto-grants-1981_01
Patent number
US04243805

Reaction notes

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