Reaktion #92088

Reaktionsgleichung

7,9,10-trimethyl-2,4-dipropyl-7-(4,8,12-trimethyl-tridecyl)-4,5,6,7-tetrahydro-1,3,8-trioxa-phenanthrene

→

(R,R,R)-5-butyl-2,7,8-trimethyl-2-(4,8,12-trimethyl-tridecyl)-chroman-6-ol

Ausbeute 105.3%

Lösungsmittel

DCM

AcOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstige(H2, 50 psi, RT)
2. 2
   Sonstigeat RT
3. 3
   Sonstigefor 16 h
4. 4
   FiltrationThe reaction mixture was then filtered through celite
5. 5
   WaschenThe celite was rinsed with DCM (2×2 mL)
6. 6
   EinengenThe DCM layer was concentrated by rotary evaporation
7. 7
   Sonstigeto yield a light brown oil
8. 8
   EinengenThe DCM was concentrated by rotary evaporation

Vorschrift

A solution of 7,9,10-trimethyl-2,4-dipropyl-7-(4,8,12-trimethyl-tridecyl)-4,5,6,7-tetrahydro-1,3,8-trioxa-phenanthrene (Ex-1C-2) (180 mg of crude material form above) in AcOH (10 mL) and conc. H2SO4 (10 drops) was hydrogenated (H2, 50 psi, RT) with 5% Pd/C (20 mg of 50% w/w wet) at RT for 16 h. The reaction mixture was then filtered through celite. The celite was rinsed with DCM (2×2 mL). The DCM layer was concentrated by rotary evaporation to yield a light brown oil. The oil was dissolved in DCM (15 mL) and passed through a silica plug. The DCM was concentrated by rotary evaporation to yield (R,R,R)-5-butyl-2,7,8-trimethyl-2-(4,8,12-trimethyl-tridecyl)-chroman-6-ol (Ex-1C-3) as a cloudy yellow oil (165 mg, >100%), which was used directly without further purification.

Quelle