Allyl Alcohol → HCID 51674883, compound

To a cooled (0° C.) solution of allyl alcohol (1.0 ml, 14.7 mmol) in chloroform (15.0 ml) was added 1.0 M diethylzinc in heptane (15.0 ml, 15.0 mmol) and stirred for 15 min under an atmosphere of nitrogen. A solution of (2R,3R)-diisopropyl 2,3-dihydroxysuccinate (2.7 ml, 12.7 mmol) was added to above mixture and stirred for 2 hours. Then another portion of 1.0 M diethylzinc in heptane (15.0 ml, 15.0 mmol) was added at 0° C. A solution of α-chloro-4-fluorobenzaldoxime (2.8 g, 16.1 mmol) in chloroform (15 ml) was added to the reaction mixture. After 3 hours, the reaction was quenched with saturated NH4Cl4, and the mixture extracted with CHCl3 (3×50 ml). The combined organic phase was washed with brine, dried over Mg2SO4, filtered, and concentrated under reduced pressure to yield a crude solid. Chromatography (1:98 to 10:90 MeOH:CH2Cl2) over silica gel yielded ((R)-3-(4-fluorophenyl)-4,5-dihydroisoxazol-5-yl)methanol, a compound of formula (22) as a white solid (2.34 g, 12.0 mmol).

1. stirringstirred for 2 hours
2. waitAfter 3 hours
3. customthe reaction was quenched with saturated NH4Cl4
4. extractionthe mixture extracted with CHCl3 (3×50 ml)
5. washThe combined organic phase was washed with brine
6. dry with materialdried over Mg2SO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customto yield a crude solid

ORD record

ord-5ed4b00c5ab84e7ab70175cc0fb0e0ef

Source dataset

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07026321B2