Sodium Iodide → 5-(4-(Iodomethyl)-2-oxabicyclo[2.2.2]octan-1-yl)-2-methyl-4-phenylthiazole

HRID 1855033Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1855033
CC1C=CC(S(O[CH2:12][C:13]23[CH2:20][CH2:19][C:16]([C:21]4[S:25][C:24]([CH3:26])=[N:23][C:22]=4[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)([CH2:17][CH2:18]2)[O:15][CH2:14]3)(=O)=O)=CC=1.[Na+].[I-:34]>CC(C)=O.C(Cl)Cl>[I:34][CH2:12][C:13]12[CH2:20][CH2:19][C:16]([C:21]3[S:25][C:24]([CH3:26])=[N:23][C:22]=3[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([CH2:17][CH2:18]1)[O:15][CH2:14]2

Komponenten

5

Edukt 2

HCID 5238Sodium IodideHCID 90408478(1-(2-Methyl-4-phenylthiazol-5-yl)-2-oxabicyclo[2.2.2]octan-4-yl)methyl 4-methylbenzenesulfonate

Produkt 1

HCID 904086535-(4-(Iodomethyl)-2-oxabicyclo[2.2.2]octan-1-yl)-2-methyl-4-phenylthiazoleAusbeute 88,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A mixture of (1-(2-Methyl-4-phenylthiazol-5-yl)-2-oxabicyclo[2.2.2]octan-4-yl)methyl 4-methylbenzenesulfonate (125 mg, 0.266 mmol) and NaI (120 mg, 0.799 mmol) in acetone (5 mL) was stirred in a seal tube at 85° C. for 18 h. The reaction was cooled to rt, diluted with DCM (5 mL), and filtered. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography on SiO2 (0-30% EtOAc:hexanes) to afford the title compound (100 mg, 88% yield) as a light yellow oil. 1H NMR (500 MHz, CDCl3) δ 7.45-7.34 (m, 5H), 3.79 (s, 2H), 2.96 (s, 2H), 2.66 (s, 3H), 2.12-2.00 (m, 2H), 1.90-1.78 (m, 2H), 1.71-1.51 (m, 4H).

Aufarbeitung

  1. temperatureThe reaction was cooled to rt
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by flash chromatography on SiO2 (0-30% EtOAc:hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-04754500108d4ed296a2bc7d12bb1192
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962660B2

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