4-Toluenesulfonyl chloride → 3-Methylbut-3-en-1-yl 4-methylbenzene-1-sulfonate

HRID 431450

反応式

HRID 431450 の反応式
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[CH:12]([OH:17])=[CH:13][CH:14]([CH3:16])[CH3:15].CCCCCC>CN(C1C=CN=CC=1)C.ClCCl>[S:1]([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)([O:17][CH2:12][CH2:13][C:14]([CH3:16])=[CH2:15])(=[O:3])=[O:2]

参加物

6

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 8058HexaneHCID 152927HCID 152927、化合物

生成物 1

HCID 3176863-Methylbut-3-en-1-yl 4-methylbenzene-1-sulfonate収率 85.3%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

2.32 mmol (442 mg) of tosyl chloride and 2.55 mmol (312 mg) of 4-(N,N-dimethylamino)pyridine are introduced while stirring with a magnetic stirrer into 5 ml of anhydrous dichloromethane in a glass reaction vessel which is equipped for handling under an inert atmosphere and has been carefully dried. 2.32 mmol (200 mg) of isopentenol dissolved in approx. 1 ml of dichloromethane are slowly added to this mixture through a septum using a syringe. The reaction is monitored by thin-layer chromatography on silica (silica gel 60 F-254; eluent: pentane/ethyl acetate 85/15 vol./vol.; Rf (product)=0.4 and Rf (TsCl)=0.5). After approx. 3 hours' stirring under a nitrogen atmosphere, the reaction mixture is diluted in a large volume of hexane (approx. 100 ml), resulting in the immediate formation of a white precipitate. The mixture is then filtered and the filtrate concentrated by evaporation under reduced pressure. The solution is then diluted with diethyl ether and refiltered. Once the solvent has evaporated, a yellowish oil is obtained. The product is purified by preparative chromatography through a silica column (silica gel 60; eluent: pentane/ethyl acetate 85/15). In this manner, 1.98 mmol (475 mg) of 3-methyl-3-butene-1-yl tosylate (85% isolated yield) are obtained. The compound (colorless oil) is stored at +4° C. in an anhydrous medium.

後処理

  1. customis equipped
  2. customhas been carefully dried
  3. additionare slowly added to this mixture through a septum
  4. customresulting in the immediate formation of a white precipitate
  5. filtrationThe mixture is then filtered
  6. concentrationthe filtrate concentrated by evaporation under reduced pressure
  7. additionThe solution is then diluted with diethyl ether
  8. customOnce the solvent has evaporated
  9. customa yellowish oil is obtained
  10. customThe product is purified by preparative chromatography through a silica column (silica gel 60; eluent: pentane/ethyl acetate 85/15)

出典と根拠

ORDレコード
ord-4e308da2ad844e1bb3086eac10fd5ff6
出典データセット
uspto-grants-2003_12
特許番号
US06660723B1

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