2-Methyl-3-butyn-2-ol → 4-(4-Cyanophenyl)-2-methyl-3-butyne-2-ol
Reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH3:10][C:11]([OH:15])([C:13]#[CH:14])[CH3:12]>[Pd].[Cu](I)I.C1(C(C2C=CC=CC=2)=C(P(C2CCCCC2)C2CCCCC2)C)C=CC=CC=1.C(NC(C)C)(C)C.CN(C)C=O>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([C:14]#[C:13][C:11]([CH3:12])([OH:15])[CH3:10])=[CH:3][CH:4]=1)#[N:7]Participants
8
Reactant 2
Product 1
Reagents, catalysts & solvents 5
Conditions
- Temperature
- 100 °C
Procedure
Into a reactor were introduced 1.38 g (10.0 mmol) of 4-chlorobenzonitrile, 1.68 g (20.0 mmol) of 2-methyl-3 butyne-2-ol, 2.7 mg (0.015 mmol) of palladium, 1.4 mg (0.0075 mmol) of copper iodide, 17.6 mg (0.045 mmol) of the 1,1-diphenyl-2-(dicyclohexylphosphine)propene obtained in Example 2, 4.0 mL (0.055 mmol) of diisopropylamine, and 4.0 ml of N,N-dimethylformamide under a nitrogen atmosphere. The resultant reaction mixture was stirred at 100° C. for 23 hours and then cooled. Thereafter, the solvent was removed under pressure. The concentrate was purified by column clromatography to obtain 1.56 g (84%) of 4-(4-cyanophenyl)-2-methyl-3-butyne-2-ol as white crystals.
Workup
- customThe resultant reaction mixture
- temperaturecooled
- customThereafter, the solvent was removed under pressure
- customThe concentrate was purified by column clromatography
Sources & evidence
- ORD record
- ord-a122b653bfe64d33b2c5ac39d09a2877
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06455720B1
Reaction notes
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