Potassium Carbonate → HCID 58951494, compound

HRID 1445750Notes

Reaction equation

HRID 1445750 reaction equation
[C:1]([Si:5]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[O:6][CH2:7][CH2:8][C:9]1[N:10]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[O:12][C:13]=1[CH3:14])([CH3:4])([CH3:3])[CH3:2].Br.Br[CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[C:1]([Si:5]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[O:6][CH2:7][CH2:8][C:9]1[N:10]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=3)=[CH:17][CH:16]=2)[O:12][C:13]=1[CH3:14])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27347202-(Bromomethyl)pyridine hydrobromideHCID 136021430HCID 136021430, compound

Product 1

HCID 58951494HCID 58951494, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-{4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-oxazol-2-yl}-phenol (1.0 g, 2.25 mmol), 2-bromomethylpyridine hydrobromide (0.85 g, 3.4 mmol), and K2CO3 (1.1 g, 7.9 mmol) in acetone (20 mL) is heated at reflux for 12 h. The mixture is filtered, and the solvent is removed in vacuo. The residue is partitioned between EtOAc and water. The organic phase is washed with water and brine, dried (Na2SO4), and concentrated. The residue is purified by flash chromatography (90 g SiO2, elute 10% to 50% EtOAc/hexane) to yield 0.97 g of the title compound. MS (ES+) 549.3

Workup

  1. temperatureis heated
  2. temperatureat reflux for 12 h
  3. filtrationThe mixture is filtered
  4. customthe solvent is removed in vacuo
  5. customThe residue is partitioned between EtOAc and water
  6. washThe organic phase is washed with water and brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe residue is purified by flash chromatography (90 g SiO2, elute 10% to 50% EtOAc/hexane)

Sources & evidence

ORD record
ord-444b49b732a84790addcc737673fd362
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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