Water → 1-(Benzyloxy)-4-[(trans)-2-nitrocyclopropyl]benzene

HRID 1023811노트

반응식

HRID 1023811 반응식
[I-].C[S+](C)(C)=O.[CH3:7]C(O)(C)C.[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23](/[CH:26]=[CH:27]/[N+:28]([O-:30])=[O:29])=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O>CS(C)=O>[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23]([C@@H:26]2[CH2:7][C@H:27]2[N+:28]([O-:30])=[O:29])=[CH:22][CH:21]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 6386tert-ButanolHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 5702926(E)-1-(Benzyloxy)-4-(2-nitrovinyl)benzene

생성물 1

HCID 666290981-(Benzyloxy)-4-[(trans)-2-nitrocyclopropyl]benzene수율 26%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

실험 절차

Trimethylsulfoxonium iodide (0.62 g, 2.82 mmol) was added in portions to a solution of t-BuOH (0.32 g, 2.82 mmol) in dry DMSO (5 mL). After 10 min a solution of 1-(benzyloxy)-4-[(E)-2-nitrovinyl]benzene (0.60 g, 2.35 mmol) in DMSO (5 mL) was transferred via canula and the mixture was stirred at room temperature for 6 h. The reaction was poured over water (10 mL) and extracted with Et2O (3×10 mL); the organic layers were washed with brine (2×15 mL), dried over anhydrous Na2SO4 and filtered. After removal of the solvent, the residual orange oil was purified by column chromatography on silica gel (5% EtOAc/hexanes) affording 0.16 g of 1-(benzyloxy)-4-[(trans)-2-nitrocyclopropyl]benzene [Rf=0.5 (20% EtOAc/hexanes), white solid, 26% yield].

후처리

  1. extractionextracted with Et2O (3×10 mL)
  2. washthe organic layers were washed with brine (2×15 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customAfter removal of the solvent
  6. customthe residual orange oil was purified by column chromatography on silica gel (5% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-d52e6ec1b39e47e4951522d9d30c2273
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722743B2

반응 노트

불러오는 중…