Methyl isobutyrate → HCID 16062603, compound

Temperature

-78 °C

Under argon gas atmosphere, 2.86 g (28 mmol) of methyl isobutyrate was dissolved in 25 ml of THF, and the solution was cooled to −78° C. To the solution was slowly added dropwise (for 10 minutes) 14.0 ml (28 mmol) of lithium diisopropylamide (Aldrich, a 2.0M heptane/THF/ethylbenzene solution thereof). While the mixture was gradually warmed (for 1 hour), the solution of 8.9 g of dimethylbismuthanyl bromide synthesized in Synthesis Example 6 in 25 ml of THF was added dropwise within the range of −40° C. to −30° C. to the mixture. Thereafter, the reaction solution was stirred until the solution temperature reached 0° C. (for 1 hour). The solids precipitated in the reaction solution were filtered off with quartz wool, THF was removed under reduced pressure, and the product was distilled under reduced pressure, giving 4.45 g of yellow oily material (46.7% yield, bp 59° C./2.0 mmHg). It was confirmed that the product was the desired one by MS (GCMS), 1H-NMR and 13C-NMR.

1. temperatureWhile the mixture was gradually warmed (for 1 hour)
2. additionwas added dropwise within the range of −40° C. to −30° C. to the mixture
3. customreached 0° C.
4. custom(for 1 hour)
5. customThe solids precipitated in the reaction solution
6. filtrationwere filtered off with quartz wool, THF
7. customwas removed under reduced pressure
8. distillationthe product was distilled under reduced pressure

ORD record

ord-4fffa48e01c344a2a80cdc22c3279bf5

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08076430B2