Triphenylphosphine → 4-[(triphenylphosphoranylidene)amino]-5-ethoxy-5H-furan-2-one

HRID 2215964노트

반응식

HRID 2215964 반응식
[N:1]([C:4]1[CH:8]([O:9][CH2:10][CH3:11])[O:7][C:6](=[O:12])[CH:5]=1)=[N+]=[N-].[C:13]1([P:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:26]1([P:19](=[N:1][C:4]2[CH:8]([O:9][CH2:10][CH3:11])[O:7][C:6](=[O:12])[CH:5]=2)([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

참가 물질

5

반응물 2

HCID 11776TriphenylphosphineHCID 219532314-azido-5-ethoxy-5H-furan-2-one

생성물 1

HCID 219532354-[(triphenylphosphoranylidene)amino]-5-ethoxy-5H-furan-2-one수율 45%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
65 °C

실험 절차

A solution of 4-azido-5-ethoxy-5H-furan-2-one (0.17 g, 1.0 mmol) and triphenylphosphine (0.26 g, 1.0 mmol) in toluene (5 mL) at room temperature under nitrogen was stirred for 1 h, then heated at 60-70° C. for 8 h. The reaction was cooled, was diluted with ethyl acetate, was washed with sodium bisulfate, sodium bicarbonate and brine, was dried over sodium sulfate and was evaporated. Purification by flash chromatography (SiO2) eluted with 1:1 ethyl acetate:hexanes afforded 4-[(triphenylphosphoranylidene)amino]-5-ethoxy-5H-furan-2-one (0.18 g, 45% yield) as an off-white solid. 1H-NMR (500 MHz, CDCl3) δ 7.73 (m, 6H), 7.65 (m, 3H), 7.55• (m, 6H), 5.58 (s, 1H), 4.33 (s, 1H), 3.81 (m, 1H), 3.64 (s, 1H), 1.27 (t, J=7.1 Hz, 3H) ppm. MS (ES+) m/e=404 (M+H).

후처리

  1. temperatureThe reaction was cooled
  2. washwas washed with sodium bisulfate, sodium bicarbonate and brine
  3. dry with materialwas dried over sodium sulfate
  4. customwas evaporated
  5. customPurification by flash chromatography (SiO2)
  6. washeluted with 1:1 ethyl acetate

출처 및 근거

ORD 기록
ord-61055952b38041c7b945850a4e0e5f71
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07109357B2

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