Triphenylphosphine → HCID 178500271, compound

HRID 976470Notes

Reaction equation

HRID 976470 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][Br:11].[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>CC#N>[CH3:1][O:2][C:3](=[O:12])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][PH:19]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1.[Br-:11]

Participants

4

Reactant 2

HCID 11776Triphenylphosphine2×HCID 11107373Methyl 8-bromooctanoate

Product 1

HCID 178500271HCID 178500271, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 8 (1.25 g, 5.23 mmol, 1.0 equiv.) in CH3CN (4.0 mL, 1.31M) was treated with triphenylphosphine (1.50 g, 5.75 mmol, 1.1 equiv.) and stirred at reflux for 10 h. Additional triphenylphosphine (0.685 g, 2.61 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 9 as a colorless foam (2.20 g, 2.61 g theoretical, 84.3%): 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), 1.62-1.43 (m, 6H, alkyl protons), 1.30-1.02 (m, 4H, alkyl protons); FABHRMS (NBA) m/e 419.2154 (C27H32BrO2P-Br- requires 419.2140).

Workup

  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

Sources & evidence

ORD record
ord-138a395c73d94c7cb9b45343979e0ff8
Source dataset
uspto-grants-1997_03
Patent number
US05612380

Reaction notes

Loading…