Reaktion #2254208

Reaktionsgleichung

O3

2,2-dimethyl-4-(4-methylphenyl)-4-(prop-2-en-1-yl)oxane

triphenylphosphine

→

2-[2,2-dimethyl-4-(4-methylphenyl)oxan-4-yl]acetaldehyde

Ausbeute 52.0%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstige(about 5 min)
2. 2
   workup.ADDITIONthe reaction mix
3. 3
   Sonstigewas purged with oxygen gas for 15 min
4. 4
   Einengenconcentrated
5. 5
   SonstigePurified by normal phase SiO2 chromatography (10 to 60% EtOAc/hexanes)

Vorschrift

O3 gas was passed through a solution of 2,2-dimethyl-4-(4-methylphenyl)-4-(prop-2-en-1-yl)oxane (1.21 g, 5 mmol) in CH2Cl2 (50 ml) at −78° C. until the solution turned light blue (about 5 min). After additional 5 minutes, the reaction mix was purged with oxygen gas for 15 min before adding triphenylphosphine (2.62 g, 10 mmol). The reaction was stirred at rt for 4 h and concentrated. Purified by normal phase SiO2 chromatography (10 to 60% EtOAc/hexanes) to give 2-[2,2-dimethyl-4-(4-methylphenyl)oxan-4-yl]acetaldehyde as a colorless oil (641 mg, 52%).

Quelle