Pentane → 10-Undecyn-1-ol

A solution of commercially available 2-[(8-bromooctyl)oxy]tetrahydro-2H-pyran (1.0 g, 3.4 mmol, 1 equiv.) in DMSO (5 ml), was added, slowly, dropwise, at r.t., under N2, to a stirred suspension of lithium acetylide ethylenediamine complex (350 mg, 3.8 mmol, 1.1 equiv.) in DMSO (5 ml). The reaction mixture was stirred at r.t. for 18 h and diluted with n-pentane (50 ml). The organic phase was washed with 1N HCl solution (2×20 ml) and water (2×20 ml), dried (Na2SO4) and evaporated to dryness under reduced pressure. The residue (colourless liquid, 570 mg, yield 70%) was dissolved in 95% EtOH (20 ml) together with p-toluenesulfonic acid (150 mg) and the mixture was heated under reflux for 2.5 h. After being cooled, the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica eluting with EtOAc/hexane (10%-30% gradient), to give the desired compound as a colourless oil (240 mg, overall yield 48%).

1. washThe organic phase was washed with 1N HCl solution (2×20 ml) and water (2×20 ml)
2. dry with materialdried (Na2SO4)
3. customevaporated to dryness under reduced pressure
4. dissolutionThe residue (colourless liquid, 570 mg, yield 70%) was dissolved in 95% EtOH (20 ml) together with p-toluenesulfonic acid (150 mg)
5. temperaturethe mixture was heated
6. temperatureunder reflux for 2.5 h
7. temperatureAfter being cooled
8. customthe solvent was evaporated under reduced pressure
9. customThe residue was purified by column chromatography on silica eluting with EtOAc/hexane (10%-30% gradient)

ORDレコード

ord-45ac9b201a444c7ea97b45b3fa1aa683

出典データセット

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08865736B2