N-methoxy-N-methyl-2-phenylbenzo[d]oxazole-6-carboxamide → 1-(2-Phenyl-benzoxazol-6-yl)butan-1-one

HRID 1481692Notes

Reaction equation

HRID 1481692 reaction equation
CON(C)[C:4]([C:6]1[CH:20]=[CH:19][C:9]2[N:10]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:12][C:8]=2[CH:7]=1)=[O:5].[CH2:22]([Mg]Cl)[CH2:23][CH3:24]>C1COCC1>[C:13]1([C:11]2[O:12][C:8]3[CH:7]=[C:6]([C:4](=[O:5])[CH2:22][CH2:23][CH3:24])[CH:20]=[CH:19][C:9]=3[N:10]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 89421776N-methoxy-N-methyl-2-phenylbenzo[d]oxazole-6-carboxamideHCID 178455855HCID 178455855, compound

Product 1

HCID 674660111-(2-Phenyl-benzoxazol-6-yl)butan-1-oneYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-methoxy-N-methyl-2-phenylbenzo[d]oxazole-6-carboxamide (1.57 g, 5.6 mmol) in THF (20 mL) was added n-PrMgCl (2.0M in ether, 4.2 mL, 8.4 mmol, 1.5 eq) at 0° C. The mixture was warmed up to room temperature then stirred for 1 h. The reaction was quenched with saturated aqueous NH4Cl then extracted with EtOAc (3×40 mL). Solvent was removed then crude product was purified by flash column chromatography (0-20% EtOAc in hexanes) to afford the title compound (1.07 g, 4.0 mmol, 72%).

Workup

  1. customThe reaction was quenched with saturated aqueous NH4Cl
  2. extractionthen extracted with EtOAc (3×40 mL)
  3. customSolvent was removed
  4. customcrude product was purified by flash column chromatography (0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b7ac9fa1e84f477c9e6ce8bdce08f91f
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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