Acetone → 2-Methylideneadamantane

Temperature

0 °C

To a suspension of methyltriphenylphosphonium bromide (14 g; 39.17 mmol) in 100 ml of ether cooled to 0° C. under argon was added dropwise n-butyllithium (2.51 g; 39.17 mmol) in hexane (15.7 mml). An ice-bath was removed and the mixture was allowed to react at room temperature for 2 hours. After cooling the reaction mixture to 0° C., a suspension of 5.35 g (35.61 mmol) of 2-adamantanone in ether (25 ml) was added and the mixture was stirred at room temperature for 2 hours. Acetone was added to decompose the phosphonium salt, the reaction mixture was filtered and the residue was washed with ether. The combined organic layer was distilled in vacuo and the residue was redissolved in ether and cooled to 0° C. to yield 3.5 g (66.4%) of 2-methylene-adamantane (see J. Org. Chem. 1985, 54, 1375) (Formula III: R2 =R3 =H; R4 and R5 together are adamantanyl), as a low melting solid.

1. customAn ice-bath was removed
2. customto react at room temperature for 2 hours
3. temperatureAfter cooling the reaction mixture to 0° C.
4. additionwas added
5. filtrationthe reaction mixture was filtered
6. washthe residue was washed with ether
7. distillationThe combined organic layer was distilled in vacuo
8. dissolutionthe residue was redissolved in ether
9. temperaturecooled to 0° C.

ORD record

ord-2211962be65c4572814046c0acd20200

Source dataset

uspto-grants-1995_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05455248