Nitrogen → trans-3,4',5-Trimethoxy-4-(trifluoromethanesulfonyloxy)stilbene

HRID 1411221

Reaktionsgleichung

Reaktionsgleichung von HRID 1411221
N#N.[CH3:3][O:4][C:5]1[CH:6]=[C:7](/[CH:14]=[CH:15]/[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH:8]=[C:9]([O:12][CH3:13])[C:10]=1[OH:11].N1C=CC=CC=1.[O:30](S(C(F)(F)F)(=O)=O)[S:31]([C:34]([F:37])([F:36])[F:35])(=O)=[O:32]>C(Cl)Cl>[CH3:3][O:4][C:5]1[CH:6]=[C:7](/[CH:14]=[CH:15]/[C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)[CH:8]=[C:9]([O:12][CH3:13])[C:10]=1[O:11][S:31]([C:34]([F:37])([F:36])[F:35])(=[O:32])=[O:30]

Komponenten

6

Edukt 4

HCID 947NitrogenHCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 442436614-Hydroxy-3,5,4'-trimethoxystilbene

Produkt 1

HCID 71812665trans-3,4',5-Trimethoxy-4-(trifluoromethanesulfonyloxy)stilbene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a round-bottomed flask (50 mL) equipped with magnetic stir bar and N2 bubbler was charged 6 (600 mg, 2 mmol), pyridine (332 mg, 4 mmol, 2 equiv) and CH2Cl2 (20 mL) The mixture was cooled in an ice bath before Tf2O (888 mg, 3 mmol, 1.5 equiv) was added dropwise over 20 min, during which the color changed from deep red to pale orange. Afterwards, the ice bath was removed and the reaction mixture was stirred at rt overnight. A work-up similar to that used in the preparation of 1a and 2a gave an oil that slowly crystallized in vacuo (790 mg, 90%). Recrystallization from heptanes/EtOAc gave compound 7 as clear, tan needles, mp. 104-106° C. (dec.). 1H NMR (CDCl3): δ 7.46 (d, J=8.7 Hz, 2H), 7.03 (d, Jab=16.1 Hz, 1H), 6.91 (d, J=8.7 Hz, 2H), 6.89 (d, Jab=16.3 Hz, 1H), 6.72 (s, 2H), 3.93 (s, 6H), 3.84 (s, 3H); 13C NMR (CDCl3): δ 160.00, 152.69, 138.64, 130.35, 129.59, 128.21, 125.75, 118.92 (q, 1JCF=321.3 Hz), 114.49, 102.94, 56.49, 55.58; 19F {13C} NMR (CDCl3): δ −74.11. Anal. Calcd for C18H17F3O6S: C, 51.67; H, 4.10. Found: C, 51.84; H, 3.97.

Aufarbeitung

  1. customTo a round-bottomed flask (50 mL) equipped with magnetic stir bar
  2. additionwas added dropwise over 20 min, during which the color
  3. customAfterwards, the ice bath was removed
  4. customA work-up similar to that used in the preparation of 1a and 2a
  5. customgave an oil that
  6. customslowly crystallized in vacuo (790 mg, 90%)
  7. customRecrystallization from heptanes/EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-98acafc346de4285b1ba811c843fc491
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921614B1

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