反応 #4617

反応方程式

3-(3,4-methylenedioxybenzoyl)pyridine

Sodium hydride

dimethyl sulfoxide

5-carboxypentyltriphenylphosphonium bromide

→

(Z)-7-(3,4-methylenedioxyphenyl)-7-(3-pyridyl)-6-heptenoic acid

収率 24.6%

溶媒

tetrahydrofuran

water

反応条件

後処理

1. 1
   温度The reaction mixture was cooled to room temperature
2. 2
   workup.STIRRINGThe mixture was stirred for 10 minutes
3. 3
   workup.ADDITIONAfter completion of addition
4. 4
   workup.STIRRINGthe mixture was further stirred at room temperature for 30 minutes
5. 5
   workup.ADDITIONwas added
6. 6
   抽出the neutral substance was extracted twice with toluene (50 ml)
7. 7
   抽出extracted with ethyl acetate
8. 8
   洗浄The organic layer was washed with water
9. 9
   乾燥dried (magnesium sulfate)
10. 10
    濃縮concentrated under reduced pressure
11. 11
    濃縮The eluate was concentrated
12. 12
    その他the residue was crystallized from ethyl acetate-isopropyl ether

実験手順

Sodium hydride (1 g, 60% in oil) was added to dimethyl sulfoxide (25 ml) under nitrogen and the mixture was heated at 85° C. with stirring for an hour. The reaction mixture was cooled to room temperature and 5-carboxypentyltriphenylphosphonium bromide (5.2 g, 11 mmoles) was added gradually. The mixture was stirred for 10 minutes and a solution of 3-(3,4-methylenedioxybenzoyl)pyridine (2.5 g, 0.11 mole) in tetrahydrofuran (10 ml) was added dropwise thereto. After completion of addition, the mixture was further stirred at room temperature for 30 minutes. After completion of the reaction, water (100 ml was added and the neutral substance was extracted twice with toluene (50 ml). The aqueous layer was adjusted to pH 5.5 with 2N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried (magnesium sulfate) and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography using ethyl acetate as the eluent. The eluate was concentrated and the residue was crystallized from ethyl acetate-isopropyl ether to give (Z)-7-(3,4-methylenedioxyphenyl)-7-(3-pyridyl)-6-heptenoic acid (0.4 g, 24.6%). Mp 90°-91° C.

出典