Toluene → 2-(Iodomethyl)-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran

Temperature

0 °C

Calcium carbonate (1.37 g, 13.7 mmol) and benzyltrimethylammonium dichloroiodate (4.04 g, 11.6 mmol) were sequentially added to a solution of toluene (20 mL)/methanol (10 mL) containing 2,3,5-trimethyl-6-(2-methylprop-2-en-1-yl)phenol (1.00 g, 5.26 mmol) synthesized in Reference Example 2 under ice-cooling condition, and the mixture was stirred at 0° C. for 30 minutes. After that, the reaction solution was concentrated under reduced pressure, and water and ethyl acetate were added to the residue to separate an organic layer. The organic layer was washed with 10% sodium sulfite aqueous solution and saturated saline, and dried using anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was purified by silica gel chromatography (hexane-ethyl acetate 100:0-95:5) to give 3.05 g of the title compound (yield: 92%).

1. customsynthesized in Reference Example 2 under ice-
2. temperaturecooling condition
3. concentrationAfter that, the reaction solution was concentrated under reduced pressure, and water and ethyl acetate
4. additionwere added to the residue
5. customto separate an organic layer
6. washThe organic layer was washed with 10% sodium sulfite aqueous solution and saturated saline
7. customdried
8. concentrationfollowed by concentration under reduced pressure
9. customThe residue was purified by silica gel chromatography (hexane-ethyl acetate 100:0-95:5)

ORD record

ord-7ae8b2ef83f54becbcd5ce6ac0577012

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08957069B2