Methylamine → 4-(2-(2,3-Dihydrobenzofuran-5-yl)-1-(4-(2-(methylamino)ethoxy)-phenyl)but-1-enyl)phenol

HRID 626208Notes

Reaction equation

Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)=[C:12]([C:15]2[CH:16]=[CH:17][C:18]3[O:22][CH2:21][CH2:20][C:19]=3[CH:23]=2)[CH2:13][CH3:14])=[CH:7][CH:6]=1.[CH3:31][NH2:32]>CO>[O:22]1[C:18]2[CH:17]=[CH:16][C:15]([C:12]([CH2:13][CH3:14])=[C:11]([C:24]3[CH:25]=[CH:26][C:27]([OH:30])=[CH:28][CH:29]=3)[C:8]3[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][NH:32][CH3:31])=[CH:6][CH:7]=3)=[CH:23][C:19]=2[CH2:20][CH2:21]1

Participants

Conditions

Temperature: 85 °C

Procedure

To a stirred solution of 4-(1-(4-(2-chloroethoxy)phenyl)-2-(2,3-dihydrobenzofuran-5-yl)but-1-enyl)phenol (500 mg, 1.0 eq) in 20 mL MeOH, 10 mL CH3NH2 (aq) was added and heated at 85° C. for 24 h. The solvent was removed in vacuo, water was added to the residue and extracted with EtOAc. The extract was dried, concentrated, and purified by column chromatography to give the desired product (Z/E=1/1). 1H NMR (400 MHz, CDCl3) δ 7.10 & 7.01 (d, J=8.8 Hz, 2H), 6.92 (s, 1H), 6.83 (d, J=8.4 Hz, 1H), 6.82 & 6.74 (d, J=8.8 Hz, 2H), 6.79 & 6.75 (d, J=8.8 Hz, 2H), 6.57 (d, J=8.4 Hz, 1H), 6.51 & 6.45 (d, J=8.8 Hz, 2H), 4.51 (t, J=8.4 Hz, 2H), 4.10 & 3.96 (t, J=4.8 Hz, 2H), 3.09 (t, J=8.8 Hz, 2H), 3.01 & 2.93 (t, J=4.8 Hz, 2H), 2.54 & 2.50 (s, 3H), 2.39-2.46 (m, 2H), 0.90-0.94 (m, 3H); m/z=416 [M+1]+.

Workup

customThe solvent was removed in vacuo, water
additionwas added to the residue
extractionextracted with EtOAc
customThe extract was dried
concentrationconcentrated
custompurified by column chromatography

Sources & evidence

ORD record: ord-b4e4481d0c3f4f2cb2003307e79e76f4
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309211B2

Reaction notes

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