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Acetic Acid → 5-(Benzyloxy)-2-(methoxycarbonyl)-1-tetralone

HRID 1271265
ノート
印刷プレビュー

反応式

HRID 1271265 の反応式
[H-].[Na+].[C:3](=[O:8])([O:6][CH3:7])OC.[CH2:9]([O:16][C:17]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:18]=1[CH2:19][CH2:20][CH2:21][C:22]2=[O:27])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(O)(=O)C>O1CCOCC1.O>[CH2:9]([O:16][C:17]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:18]=1[CH2:19][CH2:20][CH:21]([C:3]([O:6][CH3:7])=[O:8])[C:22]2=[O:27])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 176Acetic AcidHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 105869155-(Benzyloxy)-1,2,3,4-tetrahydronaphthalen-1-one

生成物 1

HCID 229320015-(Benzyloxy)-2-(methoxycarbonyl)-1-tetralone収率 98.2%

試薬・触媒・溶媒 2

HCID 962Water
溶媒
HCID 312751,4-Dioxane溶媒2 回

反応条件

温度
82.5 °C

実験手順

Under an argon atmosphere, 2.09 g of 60% sodium hydride was suspended in 30 ml of anhydrous dioxane and 11.51 g of dimethyl carbonate was added. While stirring with heating in an oil bath at 80 to 85° C., a solution of 6.58 g of 5-(benzyloxy)-1-tetralone in 15 ml of dioxane was added dropwise over about one hour. After stirring for one hour, the reaction solution was ice-cooled and 52 ml of an aqueous 1N acetic acid solution was added dropwise. The reaction solution was diluted with water, extracted with diethyl ether, washed with water and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 7.95 g of the desired compound as a pale yellow oily substance.

後処理

  1. stirringAfter stirring for one hour
  2. temperaturecooled
  3. extractionextracted with diethyl ether
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-435f2a26a0204e24ab77c276ef29e0fd
出典データセット
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07205302B2

反応ノート

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