Cesium carbonate → HCID 23590013, compound

HRID 1609912Notes

Reaction equation

HRID 1609912 reaction equation
[C:1]1([C:7]2[O:8][CH:9]=[C:10]([CH2:12][CH2:13][O:14][C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:29]([CH3:36])([CH3:35])[C:30]([O:32][CH2:33][CH3:34])=[O:31]>CN(C=O)C>[CH3:35][C:29]([O:21][C:18]1[CH:17]=[CH:16][C:15]([O:14][CH2:13][CH2:12][C:10]2[N:11]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[O:8][CH:9]=2)=[CH:20][CH:19]=1)([CH3:36])[C:30]([O:32][CH2:33][CH3:34])=[O:31]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 22261229HCID 22261229, compound

Product 1

HCID 23590013HCID 23590013, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[2-(2-Phenyloxazol-4-yl)ethoxy]phenol (3.7 g, 13.0 mmol) and cesium carbonate (4.71 g, 14.5 mmol) were suspended in anhydrous DMF (100 mL) and treated with dropwise addition of ethyl 2-bromoisobutyrate (2.54 g, 13.0 mmol, 1.93 mL). The reaction mixture was stirred at ambient temperature for 24 h and then partitioned between ether (200 mL) and 1.0 N HCl (200 mL). The organic layer was washed with water (100 mL), dried over MgSO4 and concentrated to a brown oil, which was purified by gradient column chromatography (200 mL SiO2, 100% hexanes to 20% EtOAc/hexanes) to provide 2-methyl-2-{4-[2-(2-phenyloxazol-4-yl)ethoxy]phenoxy}propionic acid, ethyl ester (2.54 g, 50%) as a colorless, viscous oil: Rf=0.5 in 20% EtOAc/hexanes; 1H NMR (250 MHz, CDCl3) δ 7.96-8.02 (m, 2H), 7.37-7.46 (m, 3H), 6.81 (s, 4H), 4.32 (q, 2H), 4.20 (t, 2H), 3.03 (t, 2H), 1.52 (s, 6H), 1.27 (t, 3H).

Workup

  1. custompartitioned between ether (200 mL) and 1.0 N HCl (200 mL)
  2. washThe organic layer was washed with water (100 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to a brown oil, which
  5. customwas purified by gradient column chromatography (200 mL SiO2, 100% hexanes to 20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-4725967440bb4eb28bebe06094b4ae8f
Source dataset
uspto-grants-2006_01
Patent number
US06982278B2

Reaction notes

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