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4-Toluenesulfonyl chloride → HCID 21024006、化合物

HRID 1446626
ノート
印刷プレビュー

反応式

HRID 1446626 の反応式
[C:1]([O:4][CH:5]1[C:6]([OH:38])([CH3:37])[CH2:7][CH2:8][CH:9]([OH:36])[CH2:10][C:11]([O:13][CH:14](/[C:19](/[CH3:35])=[CH:20]/[CH:21]=[CH:22]/[CH:23]([CH3:34])[CH2:24][CH:25]2[O:33][CH:26]2[CH:27]([CH3:32])[CH:28]([OH:31])[CH2:29][CH3:30])[CH:15]([CH3:18])[CH:16]=[CH:17]1)=[O:12])(=[O:3])[CH3:2].CN(C1C=CC=CN=1)C.[S:48](Cl)([C:51]1[CH:57]=[CH:56][C:54]([CH3:55])=[CH:53][CH:52]=1)(=[O:50])=[O:49]>ClCCl.C(OCC)(=O)C>[C:1]([O:4][CH:5]1[C:6]([OH:38])([CH3:37])[CH2:7][CH2:8][CH:9]([OH:36])[CH2:10][C:11]([O:13][CH:14](/[C:19](/[CH3:35])=[CH:20]/[CH:21]=[CH:22]/[CH:23]([CH3:34])[CH2:24][CH:25]2[O:33][CH:26]2[CH:27]([CH3:32])[CH:28]([O:31][S:48]([C:51]2[CH:57]=[CH:56][C:54]([CH3:55])=[CH:53][CH:52]=2)(=[O:50])=[O:49])[CH2:29][CH3:30])[CH:15]([CH3:18])[CH:16]=[CH:17]1)=[O:12])(=[O:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 218852-DimethylaminopyridineHCID 9807215HCID 9807215、化合物

生成物 1

HCID 21024006HCID 21024006、化合物収率 13%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate
溶媒
2 回

実験手順

A solution of (8E,12E,14E)-7-acetoxy-3,6,21-trihydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (52.3 mg, 97.4 μmol) in dichloromethane (1.0 mL) was ice-cooled, and dimethylaminopyridine (37.4 mg, 306.1 μmol) was added thereto. After stirring for about 30 min., tosyl chloride (28.6 mg, 150.0 μmol) was added and the temperature was raised to room temperature. After stirring for 4 hours, the reaction mixture was diluted with ethyl acetate (10 mL), and washed with distilled water (2 mL) for two times and with brine (2 mL). The organic layer obtained was dried over anhydrous sodium sulfate, filtered and then concentrated. The crude product was purified by medium pressure column chromatography (toluene:acetone=10:1, MERCK Lobar, LiChroprepSi 60, 4 ml/min.) and a thin layer chromatography (MERCK Silicagel 60 F254, 0.5 mm, developing solution; ethyl acetate) to obtain the title Compound (8.8 mg, 12.7 μmol, 13.0%) as a colorless oil.

後処理

  1. temperaturecooled
  2. stirringAfter stirring for 4 hours
  3. washwashed with distilled water (2 mL) for two times and with brine (2 mL)
  4. customThe organic layer obtained
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by medium pressure column chromatography (toluene:acetone=10:1, MERCK Lobar, LiChroprepSi 60, 4 ml/min.)

出典と根拠

ORDレコード
ord-396b27160d0243a38f2b3e4aaa566acc
出典データセット
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07667052B2

反応ノート

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