Sodium borohydride → HCID 12802887, compound

HRID 354587Notes

Reaction equation

HRID 354587 reaction equation
[I-].[Cl:2][C:3]1[C:4]([CH2+:17]2N(C)C(C)(C)C[O:18]2)=[C:5]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH:6]=[C:7]([Cl:9])[CH:8]=1.[BH4-].[Na+]>C(O)C.Cl.O>[Cl:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[C:5]([C:10]2[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=2)[C:4]=1[CH:17]=[O:18]

Participants

5

Reactant 1

HCID 4311764Sodium borohydride

Product 1

HCID 12802887HCID 12802887, compoundYield 82.2%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A vigorously stirred suspension of 2-(3,5-dichloro-4'-fluoro-2-[1,1'-biphenyl]yl)-3,4,4-trimethyl-2-oxazolium iodide (5.9 g, 12.3 mmol) in ethanol (50 ml) was treated portionwise with sodium borohydride (550 mg, 18 mmol). After stirring for two hours at ambient temperature the clear solution was diluted with 3 N hydrochloric acid (100 ml) and stirred on a steam bath for two hours. The reaction mixture was then cooled, diluted with H2O (200 ml) and extracted with ether (300 ml). The ether extract was washed with H2O (2×200 ml) and brine, then dried (MgSO4), filtered and evaporated in vacuo to provide 2.72 g (82%) of the title compound, mp 66°-68° C. Crystallization from petroleum ether provided an analytical sample of the title compound, mp 73°-74° C.

Workup

  1. stirringstirred on a steam bath for two hours
  2. temperatureThe reaction mixture was then cooled
  3. extractionextracted with ether (300 ml)
  4. extractionThe ether extract
  5. washwas washed with H2O (2×200 ml) and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-70ceb9d9478e4356980adf02ab23f734
Source dataset
uspto-grants-1983_03
Patent number
US04375475

Reaction notes

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