Chloromethyl Methyl Ether → HCID 86680616, compound

Temperature

0 °C

To a solution of 5-(4-(hydroxymethyl)phenyl)picolinaldehyde (0.6 g, 2.81 mmol) in DCM (15 mL) at 0° C. was added diisopropylethyl amine (1.5 mL, 8.4 mmol), followed by chloro(methoxy)methane (1.0 mL, 14.08 mmol). The reaction mixture was stirred at 0° C. for 3 h. After completion of the reaction by monitoring with TLC (30% EtOAc\hexane), the reaction mixture was extracted with dichloromethane (2×100 mL), washed with water (100 mL), dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified by a Biotage Isolera® One column purifier (silica gel 100-200μ) using 13% ethyl acetate in hexane and the product isolated as a yellow viscous liquid (0.36 g, 50% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.01 (s, 1H), 9.14 (s, 1H), 8.32 (dd, 1H), 7.996 (d, 1H), 7.83 (d, 2H), 7.50 (d, 2H), 4.67 (s, 2H), 4.60 (s, 2H), 3.28 (s, 3H); LC-MS: m/z 258.1 [M+H]+.

1. customAfter completion of the reaction
2. extractionthe reaction mixture was extracted with dichloromethane (2×100 mL)
3. washwashed with water (100 mL)
4. dry with materialdried over Na2SO4
5. concentrationconcentrated in vacuo
6. customThe resulting residue was purified by a Biotage Isolera® One column purifier (silica gel 100-200μ)

ORD record

ord-cb49db64552a46be9416736a56c51d8b

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09199975B2