HCID 11726907, compound → 5-Acetoxy-4,6-di-tert-butyl-2,2-dimethyl-2,3-dihydrobenzofuran
Reaction equation
[C:1]([O:4][C:5]1[C:10]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:9][C:8]([O:15]CC(C)=C)=[CH:7][C:6]=1[C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:3])[CH3:2]>CN(C)C1C=CC=CC=1>[C:1]([O:4][C:5]1[C:10]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:9][C:8]2[O:15][C:6]([CH3:20])([CH3:7])[CH2:5][C:7]=2[C:6]=1[C:20]([CH3:23])([CH3:21])[CH3:22])(=[O:3])[CH3:2]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
4-Acetoxy-3,5-di-tert-butyl-1-(2-methyl-2-propenyloxy)benzene (2.22 g) was dissolved in N,N-dimethylaniline (8 ml) and the solution was refluxed under a nitrogen atmosphere for 36 h. After cooling to room temperature, the reaction solution was concentrated under reduced pressure and, after addition of 1N HCl (5 ml) and diethyl ether (10 ml), stirring was continued for 15 min. The organic layer was separated and the aqueous layer was subjected to extraction with diethyl ether. The combined extracts were washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (5% ethyl acetate in n-hexane) to afford 5-acetoxy-4,6-di-tert-butyl-2,2-dimethyl-2,3-dihydrobenzofuran [1.19 g (yield, 54%)] as a white solid.