Methyl iodide → Methyl 3-methoxy-2,2-dimethylpropanoate

To a solution of 3.52 g (63 mmol) of powdered potassium hydroxide in DMSO (150 mL) are added 2 mL (16 mmol) of hydroxypivalic acid methyl ester, followed by 3.9 mL (63 mmol) of methyl iodide. The reaction mixture is stirred for 0.5 h, then quenched with water (300 mL). The reaction mixture is extracted with DCM (3×300 mL). The combined organic extracts are washed with water (2×150 mL), brine (50 mL), dried over Na2SO4 and filtered. The filtrate is concentrated under reduced pressure to yield 1.76 g of 3-methoxy-2,2-dimethyl-propionic acid methyl ester as a pale yellow oil, which is used in the next step without further purification. Yield: 77%; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.1 (6H, s), 3.2 (3H, s), 3.3 (2H, s).

1. customquenched with water (300 mL)
2. extractionThe reaction mixture is extracted with DCM (3×300 mL)
3. washThe combined organic extracts are washed with water (2×150 mL), brine (50 mL)
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationThe filtrate is concentrated under reduced pressure

ORD record

ord-fec1bee4930249d988661b3d621aa111

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08372874B2