Propargyl alcohol → 3-[3-(Methyloxy)-4-nitrophenyl]-2-propyn-1-ol
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7](Br)[CH:6]=[CH:5][C:4]=1[N+:10]([O-:12])=[O:11].[CH2:13]([OH:16])[C:14]#[CH:15].C1N2CCN(CC2)C1>C(#N)C.C(OCC)C.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:15]#[C:14][CH2:13][OH:16])[CH:6]=[CH:5][C:4]=1[N+:10]([O-:12])=[O:11]Participants
7
Conditions
- Temperature
- 60 °C
Procedure
To 5-bromo-2-nitrophenyl methyl ether (4.0 g, 17.24 mmol) in 80 mL of acetonitrile was added, Bis(tri-t-butylphosphine)palladium(0) (0.253 g, 0.5 mmol), 2-propyn-1-ol (3.33 g, 59.4 mmol), and DABCO (4.44 g, 39.6 mmol). The mixture was heated to 60° C. for 1 h. The mixture was rotovaped down and then taken up in diethyl ether. The organic layer was washed with H2O, dried (Na2SO4), filtered, and rotovaped. The crude product was purified by flash chromatography to give the title compound of step A (1.7 g, 8.2 mmol, 41%). 1H NMR (400 MHz, CDCl3) δ ppm 7.80 (d, J=8.24 Hz, 1H), 7.12 (d, J=1.65 Hz, 1H), 7.06 (dd, J=8.33, 1.56 Hz, 1H), 4.52 (s, 2H), 3.94 (s, 3H).
Workup
- washThe organic layer was washed with H2O
- dry with materialdried (Na2SO4)
- filtrationfiltered
- customThe crude product was purified by flash chromatography
Sources & evidence
- ORD record
- ord-a721f8a900ff4cab88dd976cca308c91
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08093239B2
Reaction notes
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