Downstream synthetic route of 25637-16-5

As the paragraph descriping shows that 25637-16-5 is playing an increasingly important role.

25637-16-5, 4-Bromotetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

4-Bromooxane (3.17 g, 19.2 mmol) was added drop wise to a stirred suspension of magnesium (466 mg, 19.2 mmol) and one crystal of iodine in THF (26 mL) at ambient temperature. The reaction mixture was stirred for 30 mm before it was cooled in an ice-water bath. 3-Fluoropicolinaldehyde (1.20 g, 9.59 mmol) was added drop wise. The reaction mixture was then stirred for 30 mm. The reaction mixture was quenched with saturated aqueous ammonium chloride (40 mL) and diluted with ethyl acetate (100 mL) and water (30 mL). The product was extracted into the organic phase before the layerswere separated. The aqueous layer was extracted with a second portion of ethyl acetate (50 mL), and the combined organics were dried over sodium sulfate. The volatiles were removed under reduced pressure. The cmde reaction material was purified using silica gel column chromatography. (3-Fluoropyridin-2-yl)(oxan-4-yl)methanol (1.47 g, 6.96 mmol, 73 % yield) was isolated as a colorless oil. ?H NMR (400 MHz, CDC13) 8.40-8.45 (m, 1H), 7.40-7.46 (m, 1H), 7.27-7.33 (m, 1H), 4.83-4.88 (m, 1H), 4.00 (td, J=2.14,11.37 Hz, 2H), 3.36 (ddt, J=2.20, 9.23, 11.77 Hz, 2H), 1.90-2.03 (m, 1H), 1.65-1.78 (m,1H), 1.57 (dq, J=4.65, 12.47 Hz, 1H), 1.39-1.49 (m, 2H)., 25637-16-5

As the paragraph descriping shows that 25637-16-5 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; QUESNELLE, Claude A.; HARIKRISHNAN, Lalgudi S.; HILL, Matthew D.; (180 pag.)WO2016/183114; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics