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p-Toluenesulfonic acid → (1R,5R)-10-(tetrahydropyran-2-yloxy)methyl-2-pinene

HRID 414573
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HRID 414573 반응식
[C:1]12[CH2:9][CH:5]([C:6]1([CH3:8])[CH3:7])[CH2:4][CH2:3][C:2]=2[CH3:10].[O:11]1[CH:16]=C[CH2:14][CH2:13][CH2:12]1.C1(C)C=CC(S(O)(=O)=[O:24])=CC=1.C(N([CH2:33][CH3:34])CC)C>C(Cl)Cl>[O:24]1[CH2:34][CH2:33][CH2:14][CH2:13][CH:12]1[O:11][CH2:16][CH2:10][C:2]1[C@@H:1]2[CH2:9][C@@H:5]([CH2:4][CH:3]=1)[C:6]2([CH3:8])[CH3:7]
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참가 물질

6

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 8471TriethylamineHCID 15837102(-)-Pinene

생성물 1

HCID 22840917(1R,5R)-10-(tetrahydropyran-2-yloxy)methyl-2-pinene

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of pinene (15.5 g) prepared in reference example 1 in methylene chloride (300 ml), 2,3-dihydropyran (9.4 ml) was dropped. After addition of catalytic amount of p-toluenesulphonic acid, the solution was stirred at room temperature. After reaction, triethylamine was added to the solution. The solution was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (cyclohexane: ethyl acetate=99:1) to give the title compound (20.8 g) having the following physical data:

후처리

  1. additionwas added to the solution
  2. concentrationThe solution was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (cyclohexane: ethyl acetate=99:1)

출처 및 근거

ORD 기록
ord-2546ea5de1c749aca9f70644fc75ea36
출처 데이터셋
uspto-grants-1988_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04792550

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