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

HRID 2215964ノート

反応式

HRID 2215964 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
65 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-61055952b38041c7b945850a4e0e5f71
出典データセット
uspto-grants-2006_09
特許番号
US07109357B2

反応ノート

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