3,4-dihydro-2H-pyran → 2-(4-Pentynyloxy)tetrahydro-2H-pyran

HRID 715961노트

반응식

HRID 715961 반응식
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[CH2:7]([OH:12])[CH2:8][CH2:9][C:10]#[CH:11].C(=O)(O)[O-].[Na+]>CC1C=CC(S(O)(=O)=O)=CC=1>[CH2:7]([O:12][CH:6]1[CH2:5][CH2:4][CH2:3][CH2:2][O:1]1)[CH2:8][CH2:9][C:10]#[CH:11]

참가 물질

5

반응물 3

HCID 80803,4-dihydro-2H-pyranHCID 793464-Pentyn-1-olHCID 516892Sodium Bicarbonate

생성물 1

HCID 3578162-(4-Pentynyloxy)tetrahydro-2H-pyran수율 77.2%

시약·촉매·용매 1

HCID 6101p-Toluenesulfonic acid촉매

실험 절차

3,4-Dihydro-2H-pyran (5.0 g) was added dropwise to an ice cooled mixture of 4-pentyn-1-ol (5.0 g) and 4-methylbenzenesulfonic acid (0.512 g). The resultant mixture was stirred at room temperature for 4 hours. Solid sodium bicarbonate (1.0 g) was added and the mixture was stirred for 10 minutes, then filtered and washed with diethyl ether. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-100% to give 2-(pent-4-ynyloxy)tetrahydropyran (7.72 g) as a clear oil.

후처리

  1. temperaturecooled
  2. filtrationfiltered
  3. washwashed with diethyl ether
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by chromatography on silica
  6. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-100%

출처 및 근거

ORD 기록
ord-3562ee54fdb14a73bf66059033640eed
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187494B2

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