Ethyl bromoacetate → HCID 69310455, compound

HRID 1609964Notes

Reaction equation

HRID 1609964 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([OH:24])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH2:11][C:12]1[N:13]=[C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:15][C:16]=1[CH3:17])[CH3:2].Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:30]([O:29][C:27](=[O:28])[CH2:26][O:24][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH2:10][CH2:11][C:12]2[N:13]=[C:14]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[O:15][C:16]=2[CH3:17])=[C:3]([CH2:1][CH3:2])[CH:4]=1)[CH3:31]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 22261187HCID 22261187, compound

Product 1

HCID 69310455HCID 69310455, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-ethyl-4-[2-(5-methyl-2-phenyloxazole-4-yl)ethoxy]phenol (0.29 g. 0.90 mmol), ethyl bromoacetate. (0.25 mL, 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 EtOAc (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% EtOAc/MeCl2 to give a white solid (0.25 g, 68%): 1H NMR (400 MHz, CDCl3) δ 7.97 dd, J=8.3, 2.4 Hz, 2H), 7.45-7.39 (m, 3H), 6.75 (dd, J=8.3, 2.0 Hz, 2H), 2H), 6.64 (dd, J=8.8, 3.4 Hz, 1H), 4.55 (s, 2H), 4.24 (q, J=6.5 Hz, 2H), 4.10 (t, J=6.4 Hz, 2H), 2.97 (t, J=6.6 Hz, 2H), 2.57 (t, J=7.3 Hz, 2H), 2.37 (s, 3H), 1.29 (t, J=7.3 Hz, 3H), 1.12 (t, J=6.5 Hz, 3H); MS (ES) m/e 410 (M+1).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was partitioned between EtOAc (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% EtOAc/MeCl2

Sources & evidence

ORD record
ord-c509c2f6628e4b599127f0dba1709701
Source dataset
uspto-grants-2006_01
Patent number
US06982278B2

Reaction notes

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