4-Penten-1-OL → HCID 79114386, compound

2-(Pent-4-enyloxy)acetaldehyde was prepared in a 2-step process following the literature procedures with modifications (Glaser M, et al. Bioconjugate Chem. 2008, 19, 951-957). Thus, to a stirring suspension of sodium hydride (60% in mineral oil, 2.85 g, 71.4 mmol) in THF (40 mL) under nitrogen atmosphere was added through an addition funnel a solution of 4-penten-1ol (6.15 g, 71.4 mmol) in THF (20 mL) at room temperature. After completion of addition, the mixture was refluxed for 1 h and then cooled to room temperature. A solution of bromoacetaldehyde dimethyl acetal (11.5 g, 68 mmol) in THF (40 mL) was added dropwise at room temperature over a period of 20 min. The reaction mixture was then refluxed for 4 h, cooled to room temperature, and quenched with water (20 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic solutions were washed with brine (50 mL), dried over Na2SO4 and evaporated under vacuum. The crude residue was purified by flash silica gel chromatography eluting with step gradients of 0-10% ethyl acetate in hexane to afford 5-(2,2-dimethoxy-ethoxy)-pent-1-ene (5.5 g, 31.6 mmol, 44% yield).

1. additionAfter completion of addition
2. temperaturethe mixture was refluxed for 1 h
3. temperatureThe reaction mixture was then refluxed for 4 h
4. temperaturecooled to room temperature
5. customquenched with water (20 mL)
6. customThe layers were separated
7. extractionthe aqueous layer was extracted with ethyl acetate (2×50 mL)
8. washThe combined organic solutions were washed with brine (50 mL)
9. dry with materialdried over Na2SO4
10. customevaporated under vacuum
11. customThe crude residue was purified by flash silica gel chromatography
12. washeluting with step gradients of 0-10% ethyl acetate in hexane

ORD record

ord-edc2d21cfbdc4c9e9ec700b47d74e3fe

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09056141B2