2-Methylbenzenesulfonic acid → 2H-Pyran, tetrahydro-2-(4-iodophenoxy)-

HRID 10475

Reaktionsgleichung

Reaktionsgleichung von HRID 10475
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[O:9]1[CH:14]=[CH:13][CH2:12][CH2:11][CH2:10]1.C1(C)C(S(O)(=O)=O)=CC=CC=1>C(Cl)Cl.CC1C=CC(S(O)(=O)=O)=CC=1>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14][O:9]2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 69252-Methylbenzenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 108944-Iodophenol

Produkt 1

HCID 29168032H-Pyran, tetrahydro-2-(4-iodophenoxy)-Ausbeute 92,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6101p-Toluenesulfonic acidKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a stirred solution of 4-iodophenol (11.0 g, 50 mmol) in CH2Cl2 (50 ml) cooled with an ice bath, dihydropyran (5.0 g, 60 mmol) was added dropwise over 10 min at 0–5° C. After the solution became clear, toluenesulfonic acid, TsOH, (10 mg) was added. The solution was stirred at 20° C. for 15 min. Then it was quenched by addition of NaHCO3 (1 g) and 3 drops of water, and after stirring for 5 min at 20° C., the solvent was removed in vacuo and the residue was purified by column chromatography on silica gel with petroleum ether as eluent to give 14.0 g (92%) of 1 as colorless crystal; mp 66° C.; δH(CDCl3; 300 MHz): 7.55(d, J=8.3, 2H, Ar—H), 6.83(d, J=8.4, 2H, Ar—H), 5.37(t, J=3.1, 1H, OCHO), 3.86(m, 1H, THP), 3.59(m, 1H, THP), 1.87˜1.58(m, 6H, THP).

Aufarbeitung

  1. customThen it was quenched by addition of NaHCO3 (1 g) and 3 drops of water
  2. stirringafter stirring for 5 min at 20° C.
  3. customthe solvent was removed in vacuo
  4. customthe residue was purified by column chromatography on silica gel with petroleum ether as eluent

Quellen und Nachweise

ORD-Eintrag
ord-1bb450c743ff480295cb2836392ef9e4
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094809B2

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