Methyl iodide → 3-(Bromomethyl)-3-(methoxymethyl)oxetane

To a stirring solution of (3-Bromomethyl-oxetan-3-yl)-methanol (200 mg, 1.104 mmol) in tetrahydrofuran (15 mL) at 0° C., was added sodium hydride (63 mg, 2.65 mmol) and stirred for 15 min. To this methyl iodide (629 mg, 4.419 mmol) was added to the above reaction mixture and the resultant reaction mixture was warmed to RT and stirred for 2 h. The reaction mixture was quenched with water and extracted with ethyl acetate (3×). The combined ethyl acetate layer was washed with brine and dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification by column chromatography (silica gel, 0-20% ethyl acetate in pet ether) afforded 3-(bromomethyl)-3-(methoxymethyl)oxetane as a liquid (120 mg, 55%).

1. customthe resultant reaction mixture
2. stirringstirred for 2 h
3. customThe reaction mixture was quenched with water
4. extractionextracted with ethyl acetate (3×)
5. washThe combined ethyl acetate layer was washed with brine
6. dry with materialdried over anhydrous sodium sulphate
7. concentrationconcentrated under reduced pressure
8. customPurification by column chromatography (silica gel, 0-20% ethyl acetate in pet ether)

ORD record

ord-501edffbb7ef4afb994e6a36d18a267a

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09051290B2