Triphenylphosphine → HCID 178500264, 화합물

HRID 976472노트

반응식

HRID 976472 반응식
[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]

참가 물질

4

반응물 2

HCID 11776Triphenylphosphine2회HCID 554142Methyl 9-bromononanoate

생성물 1

HCID 178500264HCID 178500264, 화합물수율 91.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c6f2b19c1a1440289099bac653c68927
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05612380

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