反应详情

(+)-γ-tocopherol (Ex-1F-1) (300 mg, 0.72 mmol), K2CO3 (199 mg, 1.44 mmol), 3-chloro-2-methyl propene (450 μL, 5.17 mmol), NaI (˜10 mg) and acetone (8 mL) were charged to a 50 mL RBF. The reaction was heated to reflux for 20 h after which time it was deemed complete by TLC (1:9 EtOAc:Hept). The reaction was diluted with water (15 mL) and DCM (10 mL). The aqueous layer was separated and washed with DCM (3×10 mL). The combined DCM layers were dried over Na2SO4, filtered and concentrated by rotary evaporation to yield (R,R,R)-2,7,8-trimethyl-6-(2-methyl-allyloxy)-2-(4,8,12-trimethyl-tridecyl)-chroman as a pale yellow liquid (Ex-1F-2) (324 mg, 95%). The isolated product was used without any further purification.

1. temperatureThe reaction was heated
2. temperatureto reflux for 20 h after which time it
3. customThe aqueous layer was separated
4. washwashed with DCM (3×10 mL)
5. dry with materialThe combined DCM layers were dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated by rotary evaporation