2-Methoxybenzaldehyde → HCID 22382435, compound

Magnesium (10.7 g) was suspended in tetrahydrofuran (80 ml), and to the suspension was added iodine (5 mg). Bromocyclopropane (32.0 ml) was added dropwise thereto over 1.5 hr and the mixture was heated under reflux for 1.5 hr. Thereto was added tetrahydrofuran to give a 1M cyclopropylmagnesium bromide-tetrahydrofuran solution. Subsequently, o-anisaldehyde (8.17 g) was dissolved in tetrahydrofuran (150 ml), the 1M cyclopropylmagnesium bromide-tetrahydrofuran solution (90 ml) was added dropwise thereto over 50 min under ice-cooling, and the mixture was stirred at room temperature for 12 hr. The reaction mixture was ice-cooled, a saturated aqueous ammonium chloride solution (9 ml) was added, and the reaction mixture was stirred at room temperature for 30 min. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=9:1) to give the title compound (6.13 g).

1. temperatureover 50 min under ice-cooling
2. temperaturecooled
3. stirringthe reaction mixture was stirred at room temperature for 30 min
4. dry with materialThe organic layer was dried over magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=9:1)

ORD record

ord-31fe12f89bdd4d58981baf700c5c4923

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07211685B2