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

HRID 2387709

반응식

HRID 2387709 반응식
[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].[O:10]1[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11]1>ClCCl.C1(C)C=CC(S(O)(=O)=O)=CC=1>[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][O:6][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][O:10]1

참가 물질

5

반응물 2

HCID 80803,4-dihydro-2H-pyranHCID 423003-Iodobenzyl alcohol

생성물 1

HCID 601336982-(3-Iodo-benzyloxy)-tetrahydro-pyran수율 103.6%

시약·촉매·용매 2

HCID 6101p-Toluenesulfonic acid촉매HCID 6344Dichloromethane용매

실험 절차

para-Toluenesulfonic acid (100 mg, cat.) was added in one portion to a cooled solution (0 C) of 3-iodobenzyl alcohol (4.71 g, 0.02 mol) and dihydropyran (1.86 g, 0.022 mol) in dichloromethane (50 mL) under a nitrogen atmosphere. The cooling bath was removed and the reaction mixture was allowed to warm to room temperature over 1 hr. Diethyl ether (100 mL) was then added followed by saturated sodium hydrogen carbonate solution (100 mL). The organic layer was separated, dried (MgSO4) and evaporated in vacuo to yield the crude product (6.59 g) A332.1, which was used immediately without further purification. HPLC YMC S-5 4.6×33 mm (2 min grad): retention time 2.16 min, no M+H+ observed.

후처리

  1. customThe cooling bath was removed
  2. additionDiethyl ether (100 mL) was then added
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-5e1c69b3fe554bd6935e24511acd51d5
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268855B2

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