Cesium carbonate → HCID 12966847, compound

HRID 2229034Notes

Reaction equation

HRID 2229034 reaction equation
[CH2:1]([C:9]1[CH:10]=[C:11]([OH:36])[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][CH2:17][C:18]1[N:19]=[C:20]([C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:26][CH:25]=2)[O:21][C:22]=1[CH3:23])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[C:38]([CH3:45])([CH3:44])[C:39]([O:41][CH2:42][CH3:43])=[O:40].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:42]([O:41][C:39](=[O:40])[C:38]([O:36][C:11]1[CH:12]=[CH:13][C:14]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:25]=[CH:26][C:27]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:28][CH:29]=3)[O:21][C:22]=2[CH3:23])=[C:9]([CH2:1][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH:10]=1)([CH3:45])[CH3:44])[CH3:43]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 22633472HCID 22633472, compound

Product 1

HCID 12966847HCID 12966847, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 3-phenethyl-4-[2-(5-methyl-2-biphenyl-4-yl-oxazole-4-yl)ethoxy]phenol (0.90 mmol), ethyl 2-bromo-2-methylpropanoate (2.25 mmol) and cesium carbonate (0.45 g, 1.38 mmol) in anhydrous DMF (4 mL) was heated for 24 h at 55° C. The mixture was concentrated in vacuo, and the residue was partitioned between ethyl acetate (50 mL) and water (40 mL), washed with brine, dried (Na2SO4), and removed in vacuo to give a crude oil which was purified using radial chromatography eluting with 2% ethyl acetate/dichloromethane to give 2-{4-[2-(2-Biphenyl-4-yl-5-methyloxazol-4-yl)ethoxy]-3-phenethylphenoxy}-2-methylpropionic acid ethyl ester. 1H NMR (400 MHz, CDCl3) δ8.03 (d, J=8.3 Hz, 2H), 7.64 (t, J=8.3 Hz, 4H), 7.46 (t, J=7.6 Hz, 2H), 7.37 (t, J=7.3 Hz, 1H), 7.26-7.17 (m, 2H), 7.13 (dd, J=12.3, 7.3 Hz, 3H), 4.24-4.19 (m, 4H), 2.98 (t, J=6.6 Hz, 2H), 2.81 (s, 4H), 2.32 (s, 3H), 1.48 (s, 6H). 1.27 (t, J=7.1 Hz, 3H), MS (ES) m/e 590 (M+1).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate (50 mL) and water (40 mL)
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. customremoved in vacuo
  6. customto give a crude oil which
  7. customwas purified
  8. washeluting with 2% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-9dc7f36031af4c8d8a140dbf8f681889
Source dataset
uspto-grants-2002_07
Patent number
US06417212B1

Reaction notes

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