2-Pyridinecarboxaldehyde → 7-(2-Pyridyl)-6-heptenoic acid

(5-Carboxypentyl)triphenyl phosphonium (13.7 g, 30.0 mmol) was suspended in tetrahydrofuran (50 ml), and potassium tert-butoxide (6.3 g, 56.0 mmol) was added thereto under ice cooling condition. The mixture was stirred for 1 hr. Successively, a solution of 2-pyridinecarbaldehyde (2.0 g, 18.7 mmol) in tetrahydrofuran (10 ml) was added to the mixture, and the mixture was stirred at 0° C. for 3 hrs. The reaction mixture was combined with 2 N aqueous sodium hydroxide solution (50 ml), washed with diethyl ether, neutralized with 6 N HCl and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated, and the residue was subjected to a silica gel (100 g) column chromatography. The fractions eluted with hexane-ethyl acetate (1:1, v/v) were collected and concentrated to give Z-form of the titled compound (2.0 g, 52%). And the fractions eluted with hexane-ethyl acetate (1:2, v/v) were collected and concentrated to give a mixture of E-form and Z-form of the titled compound (0.97 g, 25%)

1. stirringthe mixture was stirred at 0° C. for 3 hrs
2. washwashed with diethyl ether
3. extractionextracted with ethyl acetate
4. washThe organic layer was washed with saturated brine
5. dry with materialdried over magnesium sulfate
6. customThe solvent was evaporated
7. washThe fractions eluted with hexane-ethyl acetate (1:1
8. customv/v) were collected
9. concentrationconcentrated

ORDレコード

ord-7c703ced7ffc4ab3bceac4ad86613311

出典データセット

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07767665B2