Cesium carbonate → HCID 12966847, compound

HRID 398164Notes

Reaction equation

HRID 398164 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-e575c6d5ebbe4bcd840e4b397b54ce3c
Source dataset
uspto-grants-2003_08
Patent number
US06610696B2

Reaction notes

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