Tetrahydrofuran → 2-(4-Fluorophenyl)methyl-1,3-dithiane

温度

0 °C

1,3-Dithiane (20 g, 166 mmol) was dissolved in 250 mL of anhydrous THF under a nitrogen atmosphere. The resultant solution was cooled to -78° C. and n-butyllithium (128 mL of a 1.5M solution of in hexane, 199 m mol) was added. The reaction mixture was warmed to 0° C. and then stirred at 0° C. for 0.5 h. The reaction mixture was recooled to -78° C. and 25 g (0.135 mol) of 3-fluorobenzyl bromide was added over a 15 minute period. The reaction mixture was stirred for 3 h at ambient temperature and then the reaction was quenched with aqueous ammonium chloride solution. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was distilled to afford 35.5 g (94% yield) of the title compound, b.p. 125°-145° C. (0.75 mm Hg); MS DCl--NH3M/Z: 229 (M+H)+ ; 1H NMR (CDCl3) δ1.76-1.95 (1H, m), 2.05-2.19 (1H, m), 2.78-2.98 (4H, m), 2.99 (2H, d, J=9 Hz), 4.21 (1H, t, J=9 Hz), 6.93-7.05 (2H, m), 7.16-7.25 (2H, m).

1. customwas recooled to -78° C.
2. stirringThe reaction mixture was stirred for 3 h at ambient temperature
3. customthe reaction was quenched with aqueous ammonium chloride solution
4. customThe layers were separated
5. extractionthe aqueous layer was extracted with ethyl acetate
6. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. distillationThe residue was distilled

ORDレコード

ord-e05e51d0b3d34018a312b37d4ef0a1b6

出典データセット

uspto-grants-1993_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05248677