Triphenylphosphine → HCID 69118291, Verbindung

Temperatur

2.5 °C

A solution of (S)-(−)-3-chloro-1-phenyl-1-propanol (0.204 gm, 1.20 mMol), 4-acetoxy-2-methylphenol (0.200 gm, 1.20 mMol) and triphenylphosphine (0.346 g, 1.32 mMol) in 10 mL tetrahydrofuran was cooled to 0-5° C. under argon. This mixture was treated dropwise with di-isopropylazodicar-boxylate (0.26 mL, 1.32 mMol) in tetrahydrofuran (2 mL). The resulting mixture was stirred for 1 hour at 0-5° C. and was then allowed to warm to room temperature. After stirring at room temperature over night the reaction mixture was concentrated under reduced pressure and the residue triturated with 10% ethyl acetate in pentane and stirred until the suspended solid was crystalline. The suspension was filtered and the recovered crystalline solid washed with 10% ethyl acetate in pentane. The combined filtrates were concentrated under reduced pressure and the residue subjected to silica gel chromatography eluting with toluene. Fractions containing product were combined and concentrated under reduced pressure to provide 0.205 gm (54%) of the desired compound as a pale yellow oil.

1. temperatureto warm to room temperature
2. stirringAfter stirring at room temperature over night the reaction mixture
3. concentrationwas concentrated under reduced pressure
4. customthe residue triturated with 10% ethyl acetate in pentane
5. stirringstirred until the suspended solid
6. filtrationThe suspension was filtered
7. washthe recovered crystalline solid washed with 10% ethyl acetate in pentane
8. concentrationThe combined filtrates were concentrated under reduced pressure
9. washeluting with toluene
10. additionFractions containing product
11. concentrationconcentrated under reduced pressure

ORD-Eintrag

ord-0ac51c2322934f2989ce97e102694fe4

Quelldatensatz

uspto-grants-2008_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07384983B2