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p-Toluenesulfonic acid → (6-Benzenesulfonyl-3,4-dihydro-2H-naphthalen-1-ylidene)-acetic acid methyl ester

HRID 420192
ノート
印刷プレビュー

反応式

HRID 420192 の反応式
[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1(O)[C:14]2[C:9](=[CH:10][C:11]([S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:17])=[O:16])=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.CCOC(C)=O>C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:25])[CH:4]=[C:5]1[C:14]2[C:9](=[CH:10][C:11]([S:15]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)(=[O:16])=[O:17])=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 66651224(6-Benzenesulfonyl-1-hydroxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-acetic acid methyl ester

生成物 1

HCID 66650886(6-Benzenesulfonyl-3,4-dihydro-2H-naphthalen-1-ylidene)-acetic acid methyl ester収率 81.3%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

A solution of (6-benzenesulfonyl-1-hydroxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-acetic acid methyl ester (1.28 g, 3.42 mmol) and para-toluenesulfonic acid (0.50 g) in 250 mL of benzene was refluxed for 2 hours using a Dean-Stark trap. The reaction mixture was cooled and poured into 500 mL of EtOAc, and this organic phase was washed with water, saturated NaHCO3, and dried (MgSO4). Evaporation under reduced pressure gave a dark oil that was purified by elution on silica gel (hexanes:EtOAc 7:3) to yield 0.991 g (2.78 mmol, 81.2% of a white crystalline solid. MS: 357 (M+H)+.

後処理

  1. temperatureThe reaction mixture was cooled
  2. washthis organic phase was washed with water, saturated NaHCO3
  3. dry with materialdried (MgSO4)
  4. customEvaporation under reduced pressure
  5. customgave a dark oil that
  6. customwas purified by elution on silica gel (hexanes:EtOAc 7:3)

出典と根拠

ORDレコード
ord-92514b0a682d41b8b9d5656e3abc1b86
出典データセット
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08093424B2

反応ノート

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