Diisopropylamine → 1-Phenyl-1-pentyn-3-ol

Temperature

85 °C

To a degassed solution of iodobenzene (0.110 mL, 0.980 mmol), bis(triphenylphosphine)palladium(II) chloride (41.3 mg, 0.059 mmol), copper(I) iodide (9.34 mg, 0.049 mmol), and diisopropylamine (0.559 mL, 3.92 mmol) in N,N-dimethylformamide (6 mL) was added pent-1-yn-3-ol (124 mg, 1.47 mmol). The reaction mixture was heated to 85° C. for 6 h. The reaction mixture was diluted with ethyl acetate (50 mL), washed with a 10% aqueous solution of lithium chloride (10 mL), washed with a 2M aqueous ammonium hydroxide (10 mL), washed with brine (10 mL), and dried over anhydrous sodium sulfate. Concentration followed by purification by silica gel chromatography with hexanes/ethyl acetate (3/1) afforded 1-Phenylpent-1-yn-3-ol (180 mg). The compound had an HPLC ret. time=2.74 min.−Column. YMC S5 COMBISCREEN® 4.6×50 mm; Gradient time: 4 min; Flow rate=4 ml/min; Solvent A=10% MeOH−90% Water−0.2% H3PO4; Solvent B=90% MeOH−10% water−0.2% H3PO4; Start % B=0; Final % B=100.

1. washwashed with a 10% aqueous solution of lithium chloride (10 mL)
2. washwashed with a 2M aqueous ammonium hydroxide (10 mL)
3. washwashed with brine (10 mL)
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationConcentration
6. customfollowed by purification by silica gel chromatography with hexanes/ethyl acetate (3/1)

ORD record

ord-e7d4571b24ac4fb4823f4eaa6ec0e2ae

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08354398B2