Water → 1-[4-(Methoxymethoxy)phenyl]-2-phenylbutan-1-one

Temperature

0 °C

To a stirred solution of 13 (99.0 g, 0.46 mol) in anhydrous THF (750 mL) was added n-BuLi (1.6 M in hexanes, 310 mL, 0.50 mol) dropwise at −78° C. The reaction mixture was stirred for 30 min and 14 (90.1 g, 0.43 mol) dissolved in THF (500 mL) was added dropwise. The reaction mixture was stirred at −78° C. for 1 h and then slowly warmed to 0° C. H2O (500 mL) was added and the volatiles were removed under reduced pressure. The residue was extracted with Et2O (3×500 mL) and the combined extracts were washed with water (500 mL) and brine (500 mL). The mixture was dried over MgSO4 and concentrated. The residue was recrystallized from hexanes to afford 97.6 g (80%) of 15 as white needles. 1HNMR (400 MHz, DMSO-d6): δ 0.79 (t, J=7.3 Hz, 3H), 1.68 (h, J=7.0 Hz, 1H), 2.03 (h, J=7.0 Hz, 1H), 3.32 (s, 3H), 4.65 (t, J=7.3 Hz, 1H), 5.21 (s, 2H), 7.03 (d, J=8.8 Hz, 2H), 7.15 (t, J=7.1 Hz, 1H), 7.23-7.30 (m, 4H), 7.98 (d, J=8.8 Hz, 2H).

1. additionwas added dropwise
2. stirringThe reaction mixture was stirred at −78° C. for 1 h
3. customthe volatiles were removed under reduced pressure
4. extractionThe residue was extracted with Et2O (3×500 mL)
5. washthe combined extracts were washed with water (500 mL) and brine (500 mL)
6. dry with materialThe mixture was dried over MgSO4
7. concentrationconcentrated
8. customThe residue was recrystallized from hexanes

ORD record

ord-ca876288d4d643b6b27e67bd9dea86a2

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07442833B2