Chloromethyl Methyl Ether → HCID 67483162, 화합물

HRID 398656

반응식

HRID 398656 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

HCID 67483162HCID 67483162, 화합물수율 78.9%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1d04b0c2f9d045b2ad660140cb2b60bc
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610846B1

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