N-methoxy-N-methylbenzo[d]oxazole-5-carboxamide → 1-(5-Benzoxazolyl)-1-propanone

HRID 626219Notes

Reaction equation

HRID 626219 reaction equation
[CH3:1][CH2:2][Mg+].[Br-].CON(C)[C:8]([C:10]1[CH:11]=[CH:12][C:13]2[O:17][CH:16]=[N:15][C:14]=2[CH:18]=1)=[O:9]>C1COCC1>[O:17]1[C:13]2[CH:12]=[CH:11][C:10]([C:8](=[O:9])[CH2:2][CH3:1])=[CH:18][C:14]=2[N:15]=[CH:16]1

Participants

4

Reactant 2

HCID 89672883N-methoxy-N-methylbenzo[d]oxazole-5-carboxamideHCID 178461630HCID 178461630, compound

Product 1

HCID 1190847101-(5-Benzoxazolyl)-1-propanoneYield 12%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

EtMgBr (1 M, 2.0 eq, 58 mL) was added to a solution of N-methoxy-N-methylbenzo[d]oxazole-5-carboxamide (6 g, 1.0 eq) in dry THF at 0° C., Once addition was complete, the mixture was stirred for 2 h. The reaction mixture was quenched with saturated NH4Cl and extracted with EtOAc. The extract was dried, concentrated, and purified by column chromatography with petroleum ether:EtOAc=1:1 to give the desired product (0.6 g, 12%)

Workup

  1. additionOnce addition
  2. customThe reaction mixture was quenched with saturated NH4Cl
  3. extractionextracted with EtOAc
  4. customThe extract was dried
  5. concentrationconcentrated
  6. custompurified by column chromatography with petroleum ether

Sources & evidence

ORD record
ord-01a25f5cac0e4402975c8772552c9f52
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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