Triacetoxyperiodinane → Methyl 5-acetyl-4-(adamantan-1-ylmethoxy)-2-fluorobenzoate

To a mixture of methyl 4-(adamantan-1-ylmethoxy)-2-fluoro-5-(1-hydroxyethyl)benzoate (0.76 g, 2.10 mmol) in dichloromethane (20 mL) was added Dess-Martin periodinane (1.34 g, 3.20 mmol). The reaction mixture was stirred for 1 hour at ambient temperature and then quenched by addition of saturated sodium bicarbonate solution (5 mL) and saturated sodium thiosulfate solution (5 mL). Dichloromethane (30 mL) was added and the mixture was stirred for 16 hours at ambient temperature. The organic phase was separated, washed with brine (10 mL), dried over anhydrous sodium sulfate, and filtered. Concentration of the filtrate in vacuo gave a residue, which re-dissolved in a mixture of diethyl ether and dichloromethane (30 mL, 1:1). Insoluble material was filtered off, and the filtrate was concentrated in vacuo to yield the title compound as a colorless oil (0.75 g, 99%): 1H NMR (300 MHz, CDCl3) δ 8.28 (d, J=8.8 Hz, 1H), 6.62 (d, J=12.8 Hz, 1H), 3.78 (s, 3H), 3.55 (s, 2H), 2.55 (s, 3H), 1.97-1.90 (m, 3H), 1.72-1.53 (m, 12H).

1. customquenched by addition of saturated sodium bicarbonate solution (5 mL) and saturated sodium thiosulfate solution (5 mL)
2. additionDichloromethane (30 mL) was added
3. stirringthe mixture was stirred for 16 hours at ambient temperature
4. customThe organic phase was separated
5. washwashed with brine (10 mL)
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationfiltered
8. customConcentration of the filtrate in vacuo gave a residue, which
9. filtrationInsoluble material was filtered off
10. concentrationthe filtrate was concentrated in vacuo

ORD record

ord-4433fbf5505846899ff57808e7c0dae2

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952169B2