Imidazole → 4-(Tert-butyldimethylsilyloxy)-5-methoxycarbonyloxy-6-(methoxymethoxy)-3,3a,4,5,6,7-hexahydro-2,1-benzoisooxazole

HRID 1741967ノート

反応式

HRID 1741967 の反応式
[OH:1][CH:2]1[CH:7]2[CH2:8][O:9][N:10]=[C:6]2[CH2:5][CH:4]([O:11][CH2:12][O:13][CH3:14])[CH:3]1[O:15][C:16]([O:18][CH3:19])=[O:17].N1C=CN=C1.[Si:25](Cl)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]>C(Cl)Cl.C(OCC)C>[Si:25]([O:1][CH:2]1[CH:7]2[CH2:8][O:9][N:10]=[C:6]2[CH2:5][CH:4]([O:11][CH2:12][O:13][CH3:14])[CH:3]1[O:15][C:16]([O:18][CH3:19])=[O:17])([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]

参加物

6

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 677938944-Hydroxy-5-methoxycarbonyloxy-6-(methoxymethoxy)-3,3a,4,5,6,7-hexahydro-2,1-benzoisooxazole

生成物 1

HCID 678498604-(Tert-butyldimethylsilyloxy)-5-methoxycarbonyloxy-6-(methoxymethoxy)-3,3a,4,5,6,7-hexahydro-2,1-benzoisooxazole収率 73.2%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

4-Hydroxy-5-methoxycarbonyloxy-6-(methoxymethoxy)-3,3a,4,5,6,7-hexahydro-2,1-benzoisooxazole (275 mg) was dissolved in 10 ml of methylene chloride, and 200 mg of imidazole and 226 mg of tert-butyldimethylsilyl chloride were added, followed by stirring the mixture overnight at room temperature. The reaction mixture was diluted with diethyl ether, and washed with dilute hydrochloric acid, a sodium hydrogen carbonate aqueous solution and a sodium chloride aqueous solution in sequence. The organic layer was dried over anhydrous sodium sulfate, and concentration was effected under reduced pressure. The obtained residue was purified by silica gel column chromatography to give 285 mg of 4-(tert-butyldimethylsilyloxy)-5- methoxycarbonyloxy-6-(methoxymethoxy)-3,3a,4,5,6,7-hexahydro-2,1-benzoisooxazole having the following property (yield 73%).

後処理

  1. washwashed with dilute hydrochloric acid
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate, and concentration
  3. customThe obtained residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-92f0ce0b457f4d4f95767474617b631f
出典データセット
uspto-grants-1994_08
特許番号
US05334740

反応ノート

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