Potassium Carbonate → HCID 22241251, compound

HRID 892134Notes

Reaction equation

HRID 892134 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:6][CH:7]=1.[CH3:14][C:15]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][O:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([OH:33])[CH:28]=2)[C:16]=1[C:17]([O:19][CH3:20])=[O:18].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOCC>[CH3:14][C:15]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][O:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH2:2][C:3]3[N:4]=[C:5]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[O:6][CH:7]=3)[CH:28]=2)[C:16]=1[C:17]([O:19][CH3:20])=[O:18]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 35511964-(Chloromethyl)-2-phenyl-1,3-oxazoleHCID 22241441HCID 22241441, compound

Product 1

HCID 22241251HCID 22241251, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-chloromethyl-2-phenyl-oxazole (100 mg, 0.5 mmol, example 19) in DMF (2 mL) is added methyl 2-methyl-6-[(3-hydroxy-phenoxy)-methyl]-benzoate (136 mg, 0.5 mmol, example 5) followed by K2CO3 (75 mg, 0.54 mmol). The resulting mixture is heated to 60° C. and stirred at this temperature for 8 h. This mixture is then cooled to room temperature, diluted with ether, washed with water and brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (silica, 20% ethyl acetate in hexanes) to give the title compound. MS (ESI) 429 (M+H)+.

Workup

  1. temperatureThis mixture is then cooled to room temperature
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue is purified by flash chromatography (silica, 20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c1d4c13dbae74af6ae528da011efcbe9
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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