Sodium borohydride → HCID 19689353, compound

HRID 2103Notes

Reaction equation

HRID 2103 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][S:15]([C:18]([F:21])([F:20])[F:19])(=[O:17])=[O:16])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]([OH:7])[C:8]2[CH:13]=[CH:12][C:11]([CH2:14][S:15]([C:18]([F:19])([F:20])[F:21])(=[O:16])=[O:17])=[CH:10][CH:9]=2)=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 111322124-Chloro-4'-trifluoromethylsulfonylmethylbenzophenone

Product 1

HCID 19689353HCID 19689353, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

4-chloro-4'-trifluoromethylsulfonylmethylbenzophenone (5.5 g) was dispersed in methanol (200 ml). Sodium borohydride was gradually added thereto at room temperature with stirring, and the mixture was further stirred overnight at room temperature. After completion of the reaction, methanol was distilled off under reduced pressure. The residue was extracted with ethyl acetate (250 ml). The extract was washed with water and dried over anhydrous magnesium sulfate. Then, ethyl acetate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1) to obtain the desired product as a white powder (4.2 g, melting point: 113° to 115° C., yield: 77%).

Workup

  1. stirringthe mixture was further stirred overnight at room temperature
  2. distillationwas distilled off under reduced pressure
  3. extractionThe residue was extracted with ethyl acetate (250 ml)
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThen, ethyl acetate was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-0d7170f4c2ba43dc88cc7ef00696f625
Source dataset
uspto-grants-1998_03
Patent number
US05728699

Reaction notes

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