Dimethylformamide → 4-Octyloxy-benzo[1,3]dioxole

반응식

[CH2:1]1[O:5][C:4]2[CH:6]=[C:7](O)[CH:8]=[CH:9][C:3]=2[O:2]1.[H-].[Na+].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].CN(C=[O:26])C>>[CH2:14]([O:26][C:6]1[C:4]2[O:5][CH2:1][O:2][C:3]=2[CH:9]=[CH:8][CH:7]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

참가 물질

반응물 4

HCID 6228Dimethylformamide

HCID 81401-Bromooctane

HCID 24758Sodium hydride

HCID 68289Sesamol

생성물 1

HCID 685862504-Octyloxy-benzo[1,3]dioxole

실험 절차

A solution of sesamol (6.9 g; 50 mmol) in DMF (100 mL) under N2 was cooled to 0° C. and sodium hydride (60% w/w dispersion; 2.3 g; 60 mmol) carefully added. The slurry was allowed to warm to room temperature over 1 hour after which time 1-bromooctane (13 mL; 75 mmol) was added. The mixture was stirred for 5 days, poured onto H2O and extracted with diethylether (2×). The combined organic fractions were dried (MgSO4), filtered and evaporated in vacuo to yield 12.8 g (quantitative yield) of a white solid. Mp. 120° C.