Methanol → HCID 19019154, compound

To a solution of 5-(2-bromo-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-one (synthesized as instructed in Tetrahedron Letters, 1997, 38, 28, 4935) (93 mg, 0.416 mmol) in toluene (0.5 mL) were added p-TsOH.H2O (8 mg, 0.0415 mmol) and methanol (0.5 mL), followed stirring overnight at room temperature. The solution was concentrated in a vacuum, diluted with dichloromethane and washed with an aqueous saturated sodium bicarbonate solution. The organic layer thus formed was dried over sodium sulfate and filtered. The filtrate was concentrated to produce 68 mg of the compound as an oil. 1H NMR (300 MHz, CDCl3) δ 1.98 (1H, m), 2.34 (1H, m), 2.96 (1H, d), 3.56 (2H, m), 3.82 (3H, s), 4.37 (1H, pentet).

1. concentrationThe solution was concentrated in a vacuum
2. additiondiluted with dichloromethane
3. washwashed with an aqueous saturated sodium bicarbonate solution
4. customThe organic layer thus formed
5. dry with materialwas dried over sodium sulfate
6. filtrationfiltered
7. concentrationThe filtrate was concentrated

ORD record

ord-855d9b29f33845d3b89d95972e9fc1b4

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09034850B2