Diethyl Ether → HCID 86680617, compound

Temperature

0 °C

To a solution of 5-(4-((methoxymethoxy)methyl)phenyl)picolinaldehyde (0.36 g, 1.4 mmol) in THF (15 mL) at 0° C. was slowly added 3.0-M ethyl magnesium bromide in diethyl ether (1.4 mL, 4.2 mmol) was added. The reaction mixture was stirred at 0° C. for 3 h. After completion of the reaction by monitoring with TLC (50% EtOAc\hexane), the reaction mixture was quenched with sat'd. NH4Cl (50 mL) solution. The reaction mixture was extracted with EtOAc (3×50 mL), washed with water (2×50 mL), dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified by a Biotage Isolera® One column purifier (silica gel 230-400μ) using 33% ethyl acetate in hexane and the product isolated as a yellow solid (0.15 g, 37% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.76 (d, 1H), 8.04 (dd, 1H), 7.69 (d, 2H), 7.53 (d, 1H), 7.44 (d, 2H), 4.66 (s, 2H), 4.57 (s, 2H), 3.30 (s, 3H), 1.79 (m, 1H), 1.65 (m, 1H), 0.862 (t, 3H); LC-MS: m/z 288.5 [M+H]+.

1. customat 0° C.
2. additionwas added
3. customAfter completion of the reaction
4. customthe reaction mixture was quenched with sat'd
5. extractionThe reaction mixture was extracted with EtOAc (3×50 mL)
6. washwashed with water (2×50 mL)
7. dry with materialdried over Na2SO4
8. concentrationconcentrated in vacuo
9. customThe resulting residue was purified by a Biotage Isolera® One column purifier (silica gel 230-400μ)

ORD record

ord-67621a4ba3c444948bc56e2dbb77d952

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09199975B2