Potassium Carbonate → Ethyl 2-(4-methyl-3-(3-methylbut-2-enyloxy)phenylamino)oxazole-4-carboxylate

HRID 1474009Notes

Reaction equation

HRID 1474009 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[O:11][CH:12]=[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:14]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].C([O-])([O-])=O.[K+].[K+].Br[CH2:27][CH:28]=[C:29]([CH3:31])[CH3:30]>CC(C)=O>[CH3:8][C:7]1[CH:6]=[CH:5][C:4]([NH:9][C:10]2[O:11][CH:12]=[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:14]=2)=[CH:3][C:2]=1[O:1][CH2:27][CH:28]=[C:29]([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 68491443Ethyl 2-(3-hydroxy-4-methylphenylamino)oxazole-4-carboxylate

Product 1

HCID 68490366Ethyl 2-(4-methyl-3-(3-methylbut-2-enyloxy)phenylamino)oxazole-4-carboxylateYield 30%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following the general procedure for O-alkylation, Method A, a mixture of ethyl 2-(3-hydroxy-4-methylphenylamino)oxazole-4-carboxylate (118 mg, 0.45 mmol) and K2CO3 (68 mg, 0.50 mmol) in acetone (4.5 mL) was treated with 4-bromo-2-methyl-2-butene (0.063 mL, 0.54 mmol) at 60° C. Reaction control by TLC showed full conversion after 4 h. The title compound was obtained after purification by flash chromatography on silica gel (hexane:EtOAc 7/3) in 30% yield (45 mg).

Workup

  1. customReaction control by TLC
  2. customafter 4 h

Sources & evidence

ORD record
ord-16e39841f6774fcc850ea9da9deac287
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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