Methyl Acetate → HCID 58366266, compound

Temperature

-78 °C

A solution of diisopropylamine (0.241 mL, 1.72 mmol) in anhydrous THF (1.5 mL) was treated with n-BuLi (1.6 M in hexane, 0.7 mL, 1.72 mmol) at −78° C. The mixture was kept at this temperature for 1 h, and then a solution of methyl acetate (0.137 mL, 1.72 mmol) in anhydrous THF (1 mL) was added at −78° C. The reaction mixture was stirred for 1 h at −78° C., and a solution of 2-(biphenyl-4-yl)acetaldehyde (S90, 282 mg, 1.43 mmol) in anhydrous THF (2 mL) was added. The reaction mixture was stirred for another hour, then quenched by the addition of saturated aqueous NH4Cl, which was extracted with EtOAc. The combined extracts were dried over Na2SO4 and the solvent was removed under reduced pressure. Flash chromatography (SiO2, 50% Et2O-hexanes) yielded the title compound (226 mg, 58%) as a white solid: 1H NMR (CDCl3, 400 MHz) δ 7.64 (dd, 2H, J=7.2 Hz), 7.58 (dd, 2H, J=8.0 Hz), 7.49 (t, 2H, J=7.6 Hz), 7.38 (t, 1H, J=7.0 Hz), 7.34 (d, 2H, J=8.0 Hz), 4.38-4.34 (m, 1H), 3.71 (s, 3H), 3.35 (s, 1H(—OH)), 2.97-2.82 (m, 2H), 2.61-2.43 (m, 2H); 13C NMR (CDCl3, 75 MHz) δ 172.7, 140.5, 139.1, 136.6, 129.6, 128.5, 126.9, 126.7, 68.7, 51.4, 42.3, 40.3.

1. stirringThe reaction mixture was stirred for another hour
2. customquenched by the addition of saturated aqueous NH4Cl, which
3. extractionwas extracted with EtOAc
4. dry with materialThe combined extracts were dried over Na2SO4
5. customthe solvent was removed under reduced pressure

ORD record

ord-1a9e5684601e4116b2db31520ca978e3

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987312B2