3-Methoxybenzenethiol → Ethyl 2-(4-methoxyphenyl)-3-(3-methoxyphenylthio)propionate

HRID 1859353Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[CH2:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([SH:24])[CH:21]=[CH:22][CH:23]=1>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]([CH2:15][S:24][C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([O:17][CH3:16])[CH:19]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:7][CH:8]=1

Participants

Reactant 2

HCID 849893-Methoxybenzenethiol

HCID 11275761Ethyl 4-Methoxyatropate

Product 1

HCID 22123590Ethyl 2-(4-methoxyphenyl)-3-(3-methoxyphenylthio)propionate

Procedure

A process for preparing a compound of formula (6): ##STR120## characterized in that a compound of formula (1): ##STR121## is reacted with oxalic acid diethyl ester and sodium hydride to produce a compound of formula (2): ##STR122## the resulting compound of formula (2) is reacted with 3-methoxybenzenethiol represented by the formula: ##STR123## to produce a compound of formula (3): ##STR124## the resulting compound of formula (3) is reacted with hydrochloric acid to produce a compound of formula (4): ##STR125## the compound of formula formula (4) is then cyclized to produce a compound of formula (5): ##STR126## and the compound of formula (5) is reacted with methyl iodide in the presence of lithium diisopropylamide to produce the compound of formula (6).

Sources & evidence

ORD record: ord-dd0a9230405343e3875646c13bb3de54
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06153768

Reaction notes

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