Sodium hydride → HCID 10990994, compound

Following the method of Flynn and Zabrowski, J. Org. Chem. 55: 3673-3674 (1990), such reference herein incorporated by reference with regard to such synthetic teaching, diethyl allylmalonate (18.0 g, 90.0 mmol) was dissolved in tetrahydrofuran (THF) (50 mL). Sodium hydride (11.5 g, 288 mmol, 60% dispersion in oil) was added to the reaction. After 30 min of stirring at ambient temperature, a solution of N-iodosuccinimide (21.9 g, 97.2 mmol) in THF (100 mL) was added, and the reaction was stirred in the dark at ambient temperature for 15 min. The reaction was poured onto 100 g of silica gel. The contents were diluted with 400 mL of ether and stirred with a glass rod. The contents were then filtered through a bed of silica gel (100 g) in a sintered funnel. The silica gel was washed with ether (4×400 mL). The combined filtrates were concentrated by rotary evaporation to give diethyl 2-allyl-2-iodomalonate, as a yellowish orange liquid, that was used immediately in the next reaction.

1. stirringthe reaction was stirred in the dark at ambient temperature for 15 min
2. additionThe reaction was poured onto 100 g of silica gel
3. stirringstirred with a glass rod
4. filtrationThe contents were then filtered through a bed of silica gel (100 g) in a sintered funnel
5. washThe silica gel was washed with ether (4×400 mL)
6. concentrationThe combined filtrates were concentrated by rotary evaporation

ORD record

ord-9b847c784fd9406c993663d282ca9b08

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08198296B2