Hexane → HCID 53966822, compound

To a stirred solution of 3-oxetanone (0.5 g, 6.93 mmol) in dry THF (6 mL), at −78° C., under argon atmosphere, 2.5M solution of butyl lithium (BuLi) in hexane (3.05 mL, 7.62 mmol) was added dropwise over 10 min. The reaction was left to react 3 h at −78° C., then quenched with water and concentrated to dryness. The crude mixture was dissolved in CH2Cl2 and dried over Na2SO4. The organic solution was filtered and concentrated to dryness to afford a pale yellow oil (0.505 g). The crude product was purified by column chromatography using a Teledyne ISCO apparatus, eluting with Cy/TBME (from 100:0 to 70:30) affording the title compound (0.45 g, 50%) as transparent oil. 1H NMR (CDCl3): δ 0.90-1.04 (m, 3H), 1.36-1.47 (m, 4H), 1.79-1.93 (m, 2H), 4.53 (d, J=7.1, 2H), 4.59 (d, J=6.9, 2H).

1. waitThe reaction was left
2. customto react 3 h at −78° C.
3. customquenched with water
4. concentrationconcentrated to dryness
5. dissolutionThe crude mixture was dissolved in CH2Cl2
6. dry with materialdried over Na2SO4
7. filtrationThe organic solution was filtered
8. concentrationconcentrated to dryness

ORD record

ord-b6c0ed3cedef43a2859acee4a3eb8eac

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09353075B2