Triphenylphosphine → HCID 178500264、化合物

HRID 976472

反応式

HRID 976472 の反応式
[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][Br:12].[C:14]1([P:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CC#N>[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][PH:20]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1.[Br-:12]

参加物

4

反応物 2

HCID 11776Triphenylphosphine2 回HCID 554142Methyl 9-bromononanoate

生成物 1

HCID 178500264HCID 178500264、化合物収率 91.3%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of 13 (1.02 g, 4.06 mmol, 10 equiv) in CH3CN (3.5 mL 1.16M) was treated with triphenylphosphine (1.17 g, 4.47 mmol, 1.1 equiv) and stirred at reflux for 10 h. Additional triphenylphosphine (0.532 g, 2.03 mmol, 0.5 equiv) was added to the reaction mixture and stirring was continued at reflux for 5 h. The reaction mixture was concentrated under reduced pressure and washed repeatedly with Et2O (5×10 mL washes). The remaining residue was then solubilized in the minimum volume of CH2Cl2 and concentrated under reduced pressure to afford 14 as a colorless foam (1.90 g, 2.08 g theoretical, 91.3%): 1H NMR (CDCl3, 250 MHz) δ7.82-7.51 (m, 15H, ArH), 3.70-3.46 (m, 5H, CH3OC(O)R and CH2PPh3), 2.13 (t, 2H, J=7.4 Hz, CH2C(O)OCH3), 1.62-1.02 (m, 12H, alkyl protons); FABHRMS (NBA) m/e 433.2312 (C28H34BrO2P--Br- requires 433.2296).

後処理

  1. temperatureat reflux for 10 h
  2. stirringstirring
  3. temperatureat reflux for 5 h
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. washwashed repeatedly with Et2O (5×10 mL washes)
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-c6f2b19c1a1440289099bac653c68927
出典データセット
uspto-grants-1997_03
特許番号
US05612380

関連ノート

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