Iodoethane → HCID 18947544, compound

To a cold solution (0° C.) of diisopropylamine (0.80 mL, 5.7 mmol) in THF (5 mL) was added a 1.6M solution of butyllithium in hexane (3.4 mL, 5.4 mmol) over a 5 minute period and stirring was continued for an additional 45 min. Then a solution of methyl 4-chloro-2-ethyl-4-pentenoate (800 mg, 5 mmol) from Example 27, Step A, in THF (2 mL) was added and the reaction was stirred at 0° C. for another 30 minutes. Then ethyl iodide (440 μL, 5.5 mmol) was added and the reaction was allowed to proceed at room temperature for 2 hours. The reaction was quenched with NH4OAc buffer (50 mL of 25% w/v) and extracted with EtOAc. The organic layer wag separated, dried over MgSO4, filtered and concentrated. The crude product was purified by Kugelrohr distillation (b.p. 120° C. at 0.1 mm Hg) to give the title compound.

1. stirringthe reaction was stirred at 0° C. for another 30 minutes
2. waitto proceed at room temperature for 2 hours
3. customThe reaction was quenched with NH4OAc buffer (50 mL of 25% w/v)
4. extractionextracted with EtOAc
5. customThe organic layer wag separated
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. distillationThe crude product was purified by Kugelrohr distillation (b.p. 120° C. at 0.1 mm Hg)

ORD record

ord-21d46c2b18e74391be31a7463b8cc679

Source dataset

uspto-grants-1993_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05272145