Iodide Ion → HCID 86720188, compound

A solution of trimethylsulfoxium iodide (506 mg, 2.297 mmol) and potassium tert-butoxide (258 mg, 2.297 mmol) in dimethylsulfoxide (6 mL) was stirred for 1.5 hours and then transferred via syringe to a solution of methyl (3E)-2,2-dimethyl-5-oxohex-3-enoate (340 mg, 1.998 mmol) in tetrahydrofuran (6 mL). The reaction mixture was stirred for 14 hours and then partitioned between diethyl ether (25 mL) and a 5:1 v:v mixture of water:saturated aqueous sodium bicarbonate solution (12 mL). The layers were separated and the aqueous layer was extracted with diethyl ether (20 mL, 10 mL). The combined organics were washed with water (3×10 mL) and brine (10 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford methyl 2-(2-acetylcyclopropyl)-2-methylpropanoate which was carried on without further purification. MS ESI calc'd. for C10H17O3 [M+H]+ 185. found 185.

1. custompartitioned between diethyl ether (25 mL)
2. additiona 5:1 v:v mixture of water
3. customThe layers were separated
4. extractionthe aqueous layer was extracted with diethyl ether (20 mL, 10 mL)
5. washThe combined organics were washed with water (3×10 mL) and brine (10 mL)
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure

ORD record

ord-4f107f7a46fc4935b8e66d6e940649d5

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09290490B2