Methanesulfonyl chloride → Methyl 4-((methylsulfonyl)oxy)tetrahydro-2H-thiopyran-3-carboxylate

HRID 1053963

반응식

HRID 1053963 반응식
[OH:1][CH:2]1[CH2:7][CH2:6][S:5][CH2:4][CH:3]1[C:8]([O:10][CH3:11])=[O:9].CCN(C(C)C)C(C)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl.O>[CH3:21][S:22]([O:1][CH:2]1[CH2:7][CH2:6][S:5][CH2:4][CH:3]1[C:8]([O:10][CH3:11])=[O:9])(=[O:24])=[O:23]

참가 물질

6

반응물 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 10012449Methyl 4-hydroxytetrahydro-2H-thiopyran-3-carboxylate

생성물 1

HCID 10377614Methyl 4-((methylsulfonyl)oxy)tetrahydro-2H-thiopyran-3-carboxylate

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

A solution of methyl 4-hydroxytetrahydro-2H-thiopyran-3-carboxylate (3.00 g, 17.0 mmol) in DCM (170 mL) was stirred at 0° C. DIPEA (5.95 mL, 34.0 mmol) was added followed by the dropwise addition of methanesulfonyl chloride (1.95 g, 17.0 mmol). The resulting mixture was stirred at 0° C. for 30 minutes then warmed to ambient temperature and stirred for an additional 30 minutes. The mixture was carefully diluted with water and extracted with DCM (2×). The combined organic extracts were washed with 1N aqueous HCl, brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to afford the title compound. The residue was carried forward without further purification.

후처리

  1. temperaturethen warmed to ambient temperature
  2. stirringstirred for an additional 30 minutes
  3. extractionextracted with DCM (2×)
  4. washThe combined organic extracts were washed with 1N aqueous HCl, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-1626c36fd0ff46adad9d07f3cd360440
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394282B2

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