Isobutyraldehyde → Ethyl (E)-3-methylbut-1-ene-1-sulfonate

Mineral oil was removed from sodium hydride (84.4 mg, 2.110 mmol) with heptane (2×4 ml) under a nitrogen atmosphere after which anhydrous tetrahydrofuran (10 ml) was added. To this suspension was added dropwise a solution of ethyl (diethoxyphosphoryl)methanesulfonate (500 mg, 1.921 mmol) in anhydrous tetrahydrofuran (10 ml) upon which hydrogen gas evolved from the mixture. After 5 minutes a clear slightly yellow solution was obtained. Isobutyraldehyde (200 μl, 2.191 mmol) was added and the resulting mixture was stirred at room temperature over night. The reaction mixture was quenched with a mixture of brine (50 ml) and aqueous saturated ammonium chloride solution (150 ml). The aqeuous mixture was extracted with dichloromethane (3×70 ml), the combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to yield 550 mg of a slightly yellow oil that was used directly in the next step.

1. additionwas added
2. customAfter 5 minutes a clear slightly yellow solution was obtained
3. customThe reaction mixture was quenched with a mixture of brine (50 ml) and aqueous saturated ammonium chloride solution (150 ml)
4. extractionThe aqeuous mixture was extracted with dichloromethane (3×70 ml)
5. dry with materialthe combined organic layers were dried over sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customto yield 550 mg of a slightly yellow oil that

ORD record

ord-fb0feab69740415aa3f22eba96ed42e4

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08877934B2