Acetone → HCID 23107155, compound

To 2-adamantylcyclopentadiene (6.06 g, 30.3 mmol) was added 50 mL methanol, 50 mL ethanol, 20 mL tetrahydrofuran, 36 mL acetone (0.49 mol) and 0.5 mL pyrrolidine (0.006 mol). After stirring for 48 hours, 5 mL of acetic acid were injected, followed by 200 mL H2O and 200 mL diethyl ether. The organic layer was isolated and the aqueous layer extracted with diethyl ether (3×40 mL). The combined organic layers were extracted with H2O (3×25 mL) and with 10% aqueous NaOH (3×25 mL), dried over MgSO4, filtered and rotavapped. The obtained yellow solid was further purified by overnight Soxhlet extraction by 150 mL methanol. The precipitate in the filtrate was isolated by filtration at 0° C., and in vacuo drying: 4.54 g (62.5%) of 3-(2-adamantyl)-6,6-dimethylfulvene, as a yellow powder. Elemental analysis calculated for C18H24: C, 89.94; H, 10.06. Found: C, 82.23, 82.23; H, 8.78, 8.82.

1. customThe organic layer was isolated
2. extractionthe aqueous layer extracted with diethyl ether (3×40 mL)
3. extractionThe combined organic layers were extracted with H2O (3×25 mL) and with 10% aqueous NaOH (3×25 mL)
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. customThe obtained yellow solid was further purified by overnight
7. extractionSoxhlet extraction by 150 mL methanol
8. customThe precipitate in the filtrate was isolated by filtration at 0° C.
9. customin vacuo drying

ORD record

ord-84c320e10d8a46848475ceb70bb63ab0

Source dataset

uspto-grants-2004_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06693153B2