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

HRID 2387709

Reaktionsgleichung

Reaktionsgleichung von HRID 2387709
[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

Komponenten

5

Edukt 2

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

Produkt 1

HCID 601336982-(3-Iodo-benzyloxy)-tetrahydro-pyranAusbeute 103,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6101p-Toluenesulfonic acidKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-5e1c69b3fe554bd6935e24511acd51d5
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08268855B2

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