Methyl Thioglycolate → HCID 54266254, compound

HRID 1898949Notes

Reaction equation

HRID 1898949 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=1[CH:5](O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH3:13].[C:19]([O:23][CH3:24])(=[O:22])[CH2:20][SH:21]>>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=1[CH:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH3:13])[S:21][CH2:20][C:19]([O:23][CH3:24])=[O:22]

Participants

3

Reactant 2

HCID 16907Methyl ThioglycolateHCID 126802852-Methoxy-α-(2-methoxyphenyl)benzenemethanol

Product 1

HCID 54266254HCID 54266254, compoundYield 72%

Procedure

Following the procedure of Example 4, 2,2'-dimethoxybenzhydrol, synthesized in accordance with M. L. Hoefle, et. al. in J. Med. Chem. 34, 7 (1971)] is reacted with methyl thioglycolate for 3 hours at 50°-60° C. followed by 18 hours at room temperature. Chromatography on silica gel, eluting with a gradient of 10% ethyl acetate in hexane to 20% ethyl acetate in hexane, followed by additional chromatography, eluting with a gradient of 5% ethyl acetate in hexane to 10% ethyl acetate in hexane, gives methyl [[bis-(2-methoxyphenyl)methyl]thio]acetate as a white solid in 72% yield: melting point 65°-67° C.

Workup

  1. customsynthesized in accordance with M
  2. washChromatography on silica gel, eluting with a gradient of 10% ethyl acetate in hexane to 20% ethyl acetate in hexane
  3. washeluting with a gradient of 5% ethyl acetate in hexane to 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-9ae10af060624345b3196564277a293c
Source dataset
uspto-grants-1996_11
Patent number
US05571825

Reaction notes

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