3,4-dihydro-2H-pyran → 4-(Tetrahydro-pyran-2-yloxy)-cyclopent-2-enone

HRID 232229

反応式

HRID 232229 の反応式
[OH:1][CH:2]1[CH2:6][C:5](=[O:7])[CH:4]=[CH:3]1.[O:8]1[CH:13]=[CH:12][CH2:11][CH2:10][CH2:9]1.C(=O)([O-])O.[Na+]>ClCCl.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[O:7][CH:5]1[CH2:6][C:2](=[O:1])[CH:3]=[CH:4]1

参加物

6

反応物 3

HCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 41691604-Hydroxycyclopent-2-en-1-one

生成物 1

HCID 128380104-(Tetrahydro-pyran-2-yloxy)-cyclopent-2-enone収率 93.7%

試薬・触媒・溶媒 2

HCID 6101p-Toluenesulfonic acid触媒HCID 6344Dichloromethane溶媒

実験手順

In 300 ml of dichloromethane was dissolved 10 g of 4-hydroxy-2-cyclopentenone. To the solution were added 25.7 g of dihydropyran and 0.5 g of p-toluenesulfonic acid, and the mixture was stirred at room temperature for 45 minutes. The reaction solution was poured into an aqueous solution of sodium hydrogencarbonate. The organic layer was separated. The aqueous layer was further extracted with dichloromethane. The organic layers were combined, washed with a saturated aqueous saline solution, then dried (Na2SO4). The solvent was evaporated off, and the residue was subjected to a silica gel column chromatography, followed by elution with hexane--ethyl acetate (7:3) to give 17.4 g of 4-(2-tetrahydropyranyl)oxy-2-cyclopentenone as an oily product.

後処理

  1. customThe organic layer was separated
  2. extractionThe aqueous layer was further extracted with dichloromethane
  3. washwashed with a saturated aqueous saline solution
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was evaporated off
  6. washfollowed by elution with hexane--ethyl acetate (7:3)

出典と根拠

ORDレコード
ord-71408589cb3444fbb85df478f0348ffe
出典データセット
uspto-grants-1989_07
特許番号
US04851422

関連ノート

読み込み中…