Ethyl bromoacetate → HCID 69310455, compound

HRID 898466Notes

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

Conditions

Temperature: 55 °C

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

concentrationThe mixture was concentrated in vacuo
customthe residue was partitioned between EtOAc (50 mL) and water (40 mL)
washwashed with brine
dry with materialdried (Na2SO4)
customremoved in vacuo
customto give a crude oil which
customwas purified
washeluting with 2% EtOAc/MeCl2

Sources & evidence

ORD record: ord-07020d9cdeb54c6ea406207895f21854
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07351728B2

Reaction notes

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