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

HRID 260060ノート

反応式

HRID 260060 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9b29115ceef74d24b337e790c9a81ac4
出典データセット
uspto-grants-1996_06
特許番号
US05525619

反応ノート

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