4-Toluenesulfonyl chloride → 2H-Pyran, 2-(5-hexenyloxy)tetrahydro-

HRID 1494115ノート

反応式

HRID 1494115 の反応式
[CH2:1]([OH:7])[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].[O:8]1[CH:13]=[CH:12][CH2:11][CH2:10][CH2:9]1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>O1CCCC1.CCOCC>[O:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[O:7][CH2:1][CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6]

参加物

6

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 80803,4-dihydro-2H-pyranHCID 699635-Hexen-1-ol

生成物 1

HCID 111830362H-Pyran, 2-(5-hexenyloxy)tetrahydro-

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 8.5 g 5-hexen-1-ol in 100 mL tetrahydrofuran is added 14 mL dihydropyran followed by 0.5 g p-toluenesulfonyl chloride. The mixture is stirred at room temperature for 18 hours and then diluted with ether. The mixture is then washed with saturated aqueous sodium bicarbonate, dried, filtered and evaporated. The resulting oil is chromatographed over silica gel using hexane/ether (18:1) as eluent to give 6-(2-tetrahydropyranyloxy)-hex-1-ene; NMR (CDCl3): delta 5.85 (m,1H), 4.6 (brs,1H).

後処理

  1. washThe mixture is then washed with saturated aqueous sodium bicarbonate
  2. customdried
  3. filtrationfiltered
  4. customevaporated
  5. customThe resulting oil is chromatographed over silica gel

出典と根拠

ORDレコード
ord-01e4048ab9df4e4b847f85ac340b47b8
出典データセット
uspto-grants-1991_06
特許番号
US05025025

反応ノート

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