Isobutyryl chloride → HCID 12214103, compound

Ethyl isocyanoacetate (4.52 g) was added drop-wise to a stirred suspension of KOtBu in THF (35 ml) at 0° C. under nitrogen. After complete addition, the dark brown solution was stirred for 30 minutes and then a solution of isobutyryl chloride (2.1 ml) in THF (15 ml) added drop-wise, keeping the temperature below ˜10° C. The reaction was stirred for 1 hour then evaporated to dryness. The residue was treated with acetic acid (1.14 ml) and water (25 ml), and then extracted with ether (3×30 ml). The combined ether extracts were washed with saturated brine, dried over sodium sulfate, filtered and evaporated to give a brown oil that was purified by column chromatography, eluting with 1% MeOH in dichloromethane. This gave the title compound (1.91 g) as a colourless oil.

1. additionAfter complete addition
2. custombelow ˜10° C
3. stirringThe reaction was stirred for 1 hour
4. customthen evaporated to dryness
5. additionThe residue was treated with acetic acid (1.14 ml) and water (25 ml)
6. extractionextracted with ether (3×30 ml)
7. washThe combined ether extracts were washed with saturated brine
8. dry with materialdried over sodium sulfate
9. filtrationfiltered
10. customevaporated
11. customto give a brown oil that
12. customwas purified by column chromatography
13. washeluting with 1% MeOH in dichloromethane

ORD record

ord-39560b2f27d0414a997c49a299a7596c

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07691877B2