Potassium Carbonate → 5-[4-(tetrahydropyran-3-ylmethoxy)phenyl]-3-methoxyethyl-1,3,4-oxadiazol-2(3H)-one

HRID 260060노트

반응식

HRID 260060 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11](=[O:13])[N:10]([CH2:14][CH2:15][O:16][CH3:17])[N:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].S(O[CH2:29][CH:30]1[CH2:35][CH2:34][CH2:33][O:32][CH2:31]1)(=O)(=O)C>C(#N)C>[O:32]1[CH2:33][CH2:34][CH2:35][CH:30]([CH2:29][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[O:12][C:11](=[O:13])[N:10]([CH2:14][CH2:15][O:16][CH3:17])[N:9]=3)=[CH:6][CH:7]=2)[CH2:31]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 22402475Tetrahydro-2H-pyran-3-ylmethyl methanesulfonateHCID 1359905985-(4-hydroxyphenyl)-3-methoxyethyl-1,3,4-oxadiazol-2(3H)-one

생성물 1

HCID 224024735-[4-(tetrahydropyran-3-ylmethoxy)phenyl]-3-methoxyethyl-1,3,4-oxadiazol-2(3H)-one수율 24.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

2 g of 5-(4-hydroxyphenyl)-3-methoxyethyl-1,3,4-oxadiazol-2(3H)-one are dissolved in acetonitrile, followed by addition of 2.92 g of potassium carbonate and a solution of 3.12 g of 3-tetrahydropyranylmethyl mesylate in acetonitrile. The mixture is heated to reflux for 5 h and then filtered, diluted with ethyl acetate and washed with three times 50 ml of 2N sodium hydroxide. The organic phase is then washed with water until neutral, dried over sodium sulphate and filtered, and the solvent is then evaporated off. After two recrystallizations in diisopropyl ether, 0.7 g of product is obtained.

후처리

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 5 h
  3. filtrationfiltered
  4. additiondiluted with ethyl acetate
  5. washwashed with three times 50 ml of 2N sodium hydroxide
  6. washThe organic phase is then washed with water until neutral,
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. customthe solvent is then evaporated off
  10. customAfter two recrystallizations in diisopropyl ether

출처 및 근거

ORD 기록
ord-9b29115ceef74d24b337e790c9a81ac4
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05525619

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