Chloromethyl Methyl Ether → HCID 67483162, compound

HRID 398656

Reaction equation

HRID 398656 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([SH:11])=[CH:7][CH:6]=1.[CH3:13][O:14][CH2:15]Cl>C(#N)C.N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:13][O:14][CH3:15])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 7864Chloromethyl Methyl EtherHCID 14033178Methyl 2-(4-mercaptophenyl)acetate

Product 1

HCID 67483162HCID 67483162, compoundYield 78.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of (4-mercapto-phenyl)-acetic acid methyl ester (500 mg, 2.7 mmol) and chloromethyl methyl ether (331 mg, 4.1 mmol) in acetonitrile (3 mL) and pyridine (1 mL) was heated under reflux for 16 h. At this time, the reaction was concentrated in vacuo. The residue was re-dissolved in ethyl acetate (10 mL) and was washed with a 1N aqueous hydrochloric acid solution (2×25 mL) and a saturated aqueous sodium chloride solution. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 90/10 hexanes/ethyl acetate) afforded (4-methoxymethylsulfanyl-phenyl)-acetic acid methyl ester (482 mg, 77.6%) as a clear oil: EI-HRMS m/e calcd for C11H14O3S (M+) 226.0664, found 226.0664.

Workup

  1. temperatureunder reflux for 16 h
  2. concentrationAt this time, the reaction was concentrated in vacuo
  3. dissolutionThe residue was re-dissolved in ethyl acetate (10 mL)
  4. washwas washed with a 1N aqueous hydrochloric acid solution (2×25 mL)
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1d04b0c2f9d045b2ad660140cb2b60bc
Source dataset
uspto-grants-2003_08
Patent number
US06610846B1

Linked notes

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