2-Methyl-3-butyn-2-ol → 4-(3-(3-Hydroxypropyl)phenyl)-2-methylbut-3-yn-2-ol

Temperature

70 °C

To a degassed solution of 3-(3-bromophenyl)propan-1-ol (8) (0.95 g, 4.5 mmol) and 2-methyl-3-butyn-2-ol (9) (1.6 mL, 16 mmol) in triethylamine (25 mL) was added PdCl2(PPh3)3 (0.095 g, 0.14 mmol) and CuI (0.027 g, 0.14 mmol). The resulting mixture was degassed and stirred under argon at 70° C. for 15 h. The reaction mixture was concentrated under reduced pressure and diluted with EtOAc (50 mL). The solution was filtered through filter paper, washed with water (50 mL) and brine (50 mL), dried over Na2SO4 and concentrated under reduced pressure. Purification by flash chromatography (10 to 100% EtOAc-hexanes gradient) gave 4-(3-(3-hydroxypropyl)phenyl)-2-methylbut-3-yn-2-ol (10) as a light brown oil: Yield (0.78 g, 80%): 1H NMR (400 MHz, DMSO-d6) δ 7.29-7.18 (m, 4H), 5.46 (s, 1H), 4.48 (t, J=5.2 Hz, 1H), 3.38 (q, J=6.0 Hz, 2H), 2.59 (t, J=7.2 Hz, 2H), 1.66-1.73 (m, 2H), 1.46 (s, 6H).

1. customThe resulting mixture was degassed
2. concentrationThe reaction mixture was concentrated under reduced pressure
3. additiondiluted with EtOAc (50 mL)
4. filtrationThe solution was filtered
5. filtrationthrough filter paper
6. washwashed with water (50 mL) and brine (50 mL)
7. dry with materialdried over Na2SO4
8. concentrationconcentrated under reduced pressure
9. customPurification by flash chromatography (10 to 100% EtOAc-hexanes gradient)

ORD record

ord-d08bc0cd5f414af0b1a5828665cba334

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08389771B2