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4-Toluenesulfonyl chloride → 5-(Benzyloxy)-2-(methoxycarbonyl)-3,4-dihydronaphthalene

HRID 1271267
ノート
印刷プレビュー

反応式

HRID 1271267 の反応式
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][CH:13]([C:20]([O:22][CH3:23])=[O:21])[CH:14]2O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][C:13]([C:20]([O:22][CH3:23])=[O:21])=[CH:14]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=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

4

反応物 2

HCID 73974-Toluenesulfonyl chloride2 回HCID 229319625-(Benzyloxy)-1-hydroxy-2-(methoxycarbonyl)-1,2,3,4-tetrahydronaphthalene

生成物 1

HCID 229320125-(Benzyloxy)-2-(methoxycarbonyl)-3,4-dihydronaphthalene収率 49.7%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
70 °C

実験手順

To a solution of 5.96 g of 5-(benzyloxy)-1-hydroxy-2-(methoxycarbonyl)-1,2,3,4-tetrahydronaphthalene in 23 ml of anhydrous pyridine, 4.37 g of p-toluenesulfonyl chloride was added. After stirring with heating at 70° C. for 3 hours, 0.72 g of p-toluenesulfonyl chloride was further added, followed by stirring for 1.5 hours. The reaction solution was extracted with diethyl ether after adding iced water. The extract was washed in turn with water, 10% hydrochloric acid, water and an aqueous saturated sodium hydrogen carbonate solution and dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 2.79 g of the desired compound as a colorless crystal having a melting point of 64 to 67° C.

後処理

  1. stirringby stirring for 1.5 hours
  2. extractionThe reaction solution was extracted with diethyl ether
  3. additionafter adding iced water
  4. washThe extract was washed in turn with water, 10% hydrochloric acid, water
  5. dry with materialan aqueous saturated sodium hydrogen carbonate solution and dried 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-493c496a3d754fec87ce91a7b5292abd
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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