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

HRID 1411221노트

반응식

HRID 1411221 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-98acafc346de4285b1ba811c843fc491
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921614B1

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