N,N-Dimethylaniline → HCID 20823138, compound

HRID 348292Notes

Reaction equation

HRID 348292 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[C:5]([CH3:24])([O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13]CC=C)=[CH:9][CH:8]=1)[CH3:2].CN(C)[C:28]1[CH:33]=CC=C[CH:29]=1>>[CH2:1]([O:3][C:4](=[O:25])[C:5]([CH3:24])([O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([CH2:33][CH:28]=[CH2:29])[CH:8]=1)[CH3:2]

Participants

3

Reactant 2

HCID 949N,N-DimethylanilineHCID 20823144HCID 20823144, compound

Product 1

HCID 20823138HCID 20823138, compoundYield 72%

Procedure

A solution of 3-(4-allyloxyphenyl)-2-methyl-2-phenoxy-propionic acid ethyl ester (475 mg, 1.39 mmol) in dimethylaniline (1.5 mL) was heated at reflux for 18 h. After cooling to ambient temperature, the reaction mixture was partitioned between ethyl acetate and 1N H2SO4. The organic phase was dried (MgSO4), filtered and concentrated. The residue was purified by column chromatography (100 mL SiO2, hexanes to 30% ethyl acetate/hexanes) to provide the desired product (343 mg, 72%) as a pale yellow oil: 1H NMR (400 MHz, CDCl3) δ 7.23 (t, J=8.4 Hz, 2H), 7.02–6.96 (m, 3H), 6.83 (d, J=8.8 Hz, 2H), 6.72 (d, J=7.6 Hz, 1H), 6.05 (m, 1H), 5.16–5.09 (m, 2H), 4.21 (q, J=6.8 Hz, 2H), 3.38 (d, J=6.4 Hz, 2H), 3.25 (A of AB, J=13.6 Hz, 1H), 3.10 (B of AB, J=13.6 Hz, 1H), 1.41 (s, 3H), 1.23 (t, J=6.8 Hz, 3H).

Workup

  1. temperatureat reflux for 18 h
  2. customthe reaction mixture was partitioned between ethyl acetate and 1N H2SO4
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (100 mL SiO2, hexanes to 30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-32035c2cc53b4c57ab2eb87376ffaf38
Source dataset
uspto-grants-2007_02
Patent number
US07176224B2

Reaction notes

Loading…