Potassium Carbonate → HCID 70361407, compound

HRID 1199230Notes

Reaction equation

HRID 1199230 reaction equation
[CH3:1][C:2]1([CH3:18])[C@@H:4]([C:5]2[CH:6]=[N:7][C:8]([C:11]([CH3:14])([CH3:13])[CH3:12])=[N:9][CH:10]=2)[C@@H:3]1[C:15]([OH:17])=[O:16].[O:19]([C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29]Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][C:2]1([CH3:18])[C@@H:4]([C:5]2[CH:6]=[N:7][C:8]([C:11]([CH3:12])([CH3:13])[CH3:14])=[N:9][CH:10]=2)[C@@H:3]1[C:15]([O:17][CH2:29][C:28]1[CH:31]=[CH:32][CH:33]=[C:26]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:27]=1)=[O:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 945441-(Bromomethyl)-3-phenoxybenzeneHCID 18607467HCID 18607467, compound

Product 1

HCID 70361407HCID 70361407, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of trans-2,2-dimethyl-3-[2-(2-methylprop-2-yl) pyrimidin-5-yl]cyclopropane carboxylic acid (500 mg), 3-phenoxybenzylbromide (552 mg), anhydrous potassium carbonate (304 mg) and acetone (10 cm3) was heated at the reflux temperature for 2 hours with stirring after which it was kept at the ambient temperature for 16 hours. After removing the solid precipitate by filtration the filtrate was concentrated by evaporation under reduced pressure. The residual oil was subjected to high performance liquid chromatography (Gilson) using a silica column and, as eluent, a mixture of dichloromethane (100 parts by volume) and ethyl acetate (2 parts by volume). The product, 3-phenoxybenzyl trans-2,2-dimethyl-3-[2-(2-methylprop-2-yl)-pyrimidin-5-yl]cyclopropane carboxylate (800 mg) was obtained as an oil and identification was confirmed by n.m.r. and infra red spectroscopy.

Workup

  1. temperaturewas heated at the reflux temperature for 2 hours
  2. customAfter removing the solid precipitate
  3. filtrationby filtration the filtrate
  4. concentrationwas concentrated by evaporation under reduced pressure
  5. additionas eluent, a mixture of dichloromethane (100 parts by volume) and ethyl acetate (2 parts by volume)

Sources & evidence

ORD record
ord-2a717c57adb24e21b7afed09a15f783d
Source dataset
uspto-grants-1990_02
Patent number
US04898968

Reaction notes

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