Tetrahydrofuran → 4-{2-[4-(Dimethylamino)phenyl]ethenyl}benzaldehyde

Temperature

-78 °C

To a round bottom flask compound 17 (300 mg, 1 mmol) was transferred followed by THF (5 mL). The heterogeneous solution was cooled at −78° C. and n-BuLi (1.6M in hexane, 1 mmol) was added dropwise over 5 min, followed by DMF (1.5 mL). The reaction mixture was stirred at −78° C. for 3 hours then it was quenched by water (1 mL) and the mixture was extracted with ether (2×25 mL). The combined organic extracts were washed with brine, dried over MgSO4 and concentrated under reduced pressure to give compound 18. 18: 60% yield; yellow powder; 1H NMR (400 MHz, CDCl3) δ9.96 (s, 1H), 7.83 (d, 2H, J=8.2 Hz), 7.60 (d, 2H, J=8.2 Hz), 7.44 (d, 2H, J=8.8 Hz), 7.22 (d, 1H, J=16.2 Hz), 6.94 (d, 1H, J=16.2 Hz), 6.72 (d, 2H, J=8.8 Hz), 3.01 (s, 6H); 13C NMR (100 MHz, CDCl3) δ 191.8, 150.8, 144.7, 134.7, 134.6, 132.7, 130.4, 128.4, 126.4, 124.9, 122.8, 112.4, 40.5; HRMS calc for C17H17NO 252.1384 found 252.1383.

1. customit was quenched by water (1 mL)
2. extractionthe mixture was extracted with ether (2×25 mL)
3. washThe combined organic extracts were washed with brine
4. dry with materialdried over MgSO4
5. concentrationconcentrated under reduced pressure

ORD record

ord-df01ea7bb0264fc6972fb0c9215d417a

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08940918B2