3,4-dihydro-2H-pyran → 2-But-3-enoxyoxane

HRID 1887418

反応式

HRID 1887418 の反応式
[CH2:1]([OH:5])[CH2:2][CH:3]=[CH2:4].[O:6]1[CH:11]=[CH:10][CH2:9][CH2:8][CH2:7]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClCCl>[CH2:1]([O:5][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][O:6]1)[CH2:2][CH:3]=[CH2:4]

参加物

5

反応物 3

HCID 80803,4-dihydro-2H-pyranHCID 693893-Buten-1-olHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

生成物 1

HCID 3199452-But-3-enoxyoxane収率 89%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

In a 1000 ml rb flask were placed 3-buten-1-ol (7.21 g, 100.00 mmol), 3,4-dihydro-2H-pyran (12.62 g, 150.00 mmol) and pyridinium p-toluenesulfonate (2.51 g, 10.00 mmol) in 350 ml of anhydrous dichloromethane. The reaction mixture was stirred at room temperature for 4 h. Then the reaction mixture was concentrated and the residue was purified by column with Hexane/Ethyl acetate=100/5 to provide 13.90 g of the desired product as an oil (89.0%). 1H-NMR (DMSO-d6) δ 5.851-5.742 (m, 1H), 5.103-5.011 (d, 1H), 4.997-4.985 (d, 1H), 4.555-4.537 (t, 1H), 3.745-3.611 (m, 2H), 3.433-3.347 (m, 2H), 2.290-2.236 (m, 2H), 1.698-1.675 (m, 2H), 1.611-1.566 (m, 4H).

後処理

  1. customIn a 1000 ml rb flask were placed
  2. concentrationThen the reaction mixture was concentrated
  3. customthe residue was purified by column with Hexane/Ethyl acetate=100/5

出典と根拠

ORDレコード
ord-b9887947d73e43e8bac1958882e96144
出典データセット
uspto-grants-2013_08
特許番号
US08501755B2

関連ノート

読み込み中…