N,N-Dimethylaniline → HCID 20823138, compound

HRID 1393408Notes

Reaction equation

HRID 1393408 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 EtOAc 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% EtOAc/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 EtOAc 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% EtOAc/hexanes)

Sources & evidence

ORD record
ord-8579d6cb454a46a48ac9b10ab58cd892
Source dataset
uspto-grants-2008_03
Patent number
US07345070B2

Reaction notes

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