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

HRID 232229

반응식

HRID 232229 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6101p-Toluenesulfonic acid촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-71408589cb3444fbb85df478f0348ffe
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04851422

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