反应详情

(+)-γ-tocopherol (Ex-1D-1) (300 mg, 0.72 mmol), K2CO3 (199 mg, 1.44 mmol), allyl bromide (182 μL, 1.44 mmol) 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 (1:5 EtOAc:Hept). The reaction was diluted with water (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 a pale yellow oil. The oil was flashed through a silica plug (1:1: DCM:Heptane). After concentration of the eluent, (R,R,R)-6-allyloxy-2,7,8-trimethyl-2-(4,8,12-trimethyl-tridecyl)-chroman (Ex-1D-2) was obtained as a clear, colorless oil (334 mg, >100%), which was used without 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
8. customto yield a pale yellow oil