Diethyl Ether → 3,3-Difluoro-4-methylpentane-1,4-diol

Temperature

25 °C

To a solution of 311 mL of 1.6 M ethereal methyllithium (0.498 mol) of 0° was added dropwise 11.16 g (0.066 mol) of ethyl 2,2-difluoro-4-hydroxybutanoate in 150 mL of ether. The mixture was stirred at 0° C. for 1 hr and at 25° C. for 17 hr. The mixture was quenched by adding 14 mL of saturated brine at 0° C. The mixture was poured into saturated brine and the product was isolated with ether. The ether layers were dried over anhydrous magnesium sulfate, filtered, and evaporated to dryness. The residue was chromatographed on 0.06-0.20 mm of silica gel to give 4-methyl-3,3-difluoro-1,4-pentanediol. NMR (CDCl3) δ3.84 (triplet, 2, J=6 Hz), 2.75 (broad, OH), 2.22 (multiplet, 2), and 1.31 ppm (triplet, 6, J=1 Hz).

1. customThe mixture was quenched
2. additionby adding 14 mL of saturated brine at 0° C
3. additionThe mixture was poured into saturated brine
4. customthe product was isolated with ether
5. dry with materialThe ether layers were dried over anhydrous magnesium sulfate
6. filtrationfiltered
7. customevaporated to dryness
8. customThe residue was chromatographed on 0.06-0.20 mm of silica gel

ORD record

ord-724ae6bdaf0347ce9bf1876b8eecb95a

Source dataset

uspto-grants-1983_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04397847