Sodium borohydride → HCID 67331099, compound

HRID 1896760Notes

Reaction equation

HRID 1896760 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([CH:17]([OH:19])[CH3:18])=[CH:13][C:11]=3[N:12]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67332535HCID 67332535, compound

Product 1

HCID 67331099HCID 67331099, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)ethanone (150 mg, 0.55 mmol) in tetrahydrofuran at 0° C. was added sodium borohydride (52 mg, 1.38 mmol). The resulting mixture was stirred at room temperature for 16 h. The reaction was then quenched at 0° C. with 1M hydrochloric acid solution and extracted three times with ethyl acetate. The combined organic layers were dried over anhydrous MgSO4 and evaporated. The resulting solid was purified by column chromatography eluting using a gradient (ethyl acetate/hexanes 1:3 v/v to ethyl acetate/hexanes 1:2 v/v) to afford 81.7 mg (54%) of the title compound. (LCMS RT=6.47 min, MH+ 274.0)

Workup

  1. customThe reaction was then quenched at 0° C. with 1M hydrochloric acid solution
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  4. customevaporated
  5. customThe resulting solid was purified by column chromatography
  6. washeluting

Sources & evidence

ORD record
ord-c9d5480df6124eeea12f02ea38632190
Source dataset
uspto-grants-2013_08
Patent number
US08518980B2

Reaction notes

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