Tetrahydrofuran → HCID 66891637, compound

To a solution of methyl 5-fluoro-2,3-bis{[2-(methyloxy)ethyl]oxy}benzoate (0.34 g, 1.13 mmol) at 0° C. was added a solution of lithium aluminum hydride in tetrahydrofuran (1M, 1.2 mL, 1.2 mmol) and the resulting mixture was stirred for one hour. It was then quenched with ethyl acetate (1 mL) and 5% sodium hydroxide solution (1 mL), diluted with ether (100 mL), and filtered. The filtrate was washed water and brine (100 mL each), dried over sodium sulfate, filtered and concentrated to give (5-fluoro-2,3-bis{[2-(methyloxy)ethyl]oxy}phenyl)methanol (0.30 g, 1.10 mmol, 97% yield), 1H NMR (400 MHz, CDCl3): 6.63-6.59 (m, 2H), 4.58-4.56 (d, 2H), 4.29-4.24 (m, 2H), 4.14-4.10 (m, 2H), 3.77-3.69 (m, 4H), 3.44 (s, 3H), 3.42 (s, 3H).

1. customIt was then quenched with ethyl acetate (1 mL) and 5% sodium hydroxide solution (1 mL)
2. additiondiluted with ether (100 mL)
3. filtrationfiltered
4. washThe filtrate was washed water and brine (100 mL each)
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-3aa13770c26342ec9c4b45d5198923f4

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07872014B2