Methylamine → 4-(1-(4-Hydroxyphenyl)-1-(4-(2-(methylamino)ethoxy)phenyl)-but-1-en-2-yl)-2-methoxyphenol

HRID 626127Notes

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

Participants

Conditions

Temperature: 85 °C

Procedure

To a stirred solution of 4-(1-(4-(2-Chloroethoxy)phenyl)-1-(4-hydroxyphenyl)-but-1-en-2-yl)-2-methoxyphenol (88 mg, impure) in 10 mL MeOH was added 2 mL CH3NH2 (aq). After the mixture was heated at 85° C. for 24 h., the solvent was removed in vacuo, EtOAc was added, the mixture was washed with water and brine, dried over Na2SO4, filtered and the filtrate was evaporated in vacuo. The residue was purified by column chromatography (CH2Cl2/MeOH(NH3 gas)=10/1) to give the desired product (42 mg, 48% yield, Z/E=1/1) as a white solid. m/z=420[M+1]+.

Workup

customthe solvent was removed in vacuo, EtOAc
additionwas added
washthe mixture was washed with water and brine
dry with materialdried over Na2SO4
filtrationfiltered
customthe filtrate was evaporated in vacuo
customThe residue was purified by column chromatography (CH2Cl2/MeOH(NH3 gas)=10/1)

Sources & evidence

ORD record: ord-aaeb73f7392146a596631b0e3f77081e
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309211B2

Reaction notes

Loading…