Water → 5-Acetoxy-4,6-di-tert-butyl-2,2-diethyl-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]([OH:15])=[C:7]([CH:16]=[C:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[C:6]=1[C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:3])[CH3:2].B(F)(F)F.O>ClCCl>[C:1]([O:4][C:5]1[C:10]([C:11]([CH3:12])([CH3:13])[CH3:14])=[CH:9][C:8]2[O:15][C:17]([CH2:20][CH3:21])([CH2:18][CH3:19])[CH2:16][C:7]=2[C:6]=1[C:22]([CH3:23])([CH3:24])[CH3:25])(=[O:3])[CH3:2]Participants
5
Procedure
4-Acetoxy-3,5-di-tert-butyl-2-(2-ethyl-1-butenyl)phenol (0.85 g, 2.5 mmol) was dissolved in dichloromethane (10 ml) and BF3 etherate (0.4 ml) was added dropwise to the solution under a nitrogen atmosphere. After stirring at room temperature for 3 h, water was added to the reaction mixture and extracted with ethyl acetate. The extracted layer was washed with a saturated aqueous solution of sodium hydrogen carbonate, dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane) to afford 5-acetoxy-4,6-di-tert-butyl-2,2-diethyl-2,3-dihydrobenzofuran [0.45 g (yield, 53%)] as a pale yellow oil. Mass 346(M+), 304, 57
Workup
- extractionextracted with ethyl acetate
- washThe extracted layer was washed with a saturated aqueous solution of sodium hydrogen carbonate
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
- customThe concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane)
Sources & evidence
- ORD record
- ord-b0e4508a0cef4d8494d2f35bf9828cbd
- Source dataset
- uspto-grants-1996_11
- Patent number
- US05574178
Reaction notes
Loading…