Sodium Iodide → 4-(Iodomethyl)-1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octane

HRID 1855083Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1855083
CC1C=CC(S(O[CH2:12][C:13]23[CH2:20][CH2:19][C:16]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[CH:22]=4)([CH2:17][CH2:18]2)[O:15][CH2:14]3)(=O)=O)=CC=1.[Na+].[I-:35]>CC#N>[I:35][CH2:12][C:13]12[CH2:20][CH2:19][C:16]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH:22]=3)([CH2:17][CH2:18]1)[O:15][CH2:14]2

Komponenten

4

Edukt 2

HCID 5238Sodium IodideHCID 90408232(1-(3-Phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)methyl 4-methylbenzenesulfonate

Produkt 1

HCID 904081314-(Iodomethyl)-1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octaneAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of (1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)methyl 4-methylbenzenesulfonate (1G; 950 mg, 2.05 mmol) and NaI (3.07 g, 20.45 mmol) in MeCN (10 mL) was heated to 70° C. for 72 h. The reaction mixture was cooled to rt, filtered and concentrated in vacuo. The residual crude product was purified by flash chromatography to give the title compound (745 mg, 1.77 mmol; 87% yield) as a white solid. LCMS, [M+H]+=421; 1H NMR (400M Hz, CDCl3) δ 7.38-7.23 (m, 3H), 7.19-7.08 (m, 3H), 7.04-6.98 (m, 2H), 6.87 (ddd, J=8.0, 2.3, 1.0 Hz, 1H), 3.88 (s, 2H), 3.07 (s, 2H), 2.18-1.95 (m, 4H), 1.87-1.68 (m, 4H).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to rt
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe residual crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f73413eaf3b549e7ace0b011a5d0498f
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962660B2

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