Reaktion #157896

Reaktionsgleichung

ammonium chloride

n-butyllithium

(4-bromophenyl)(cyclopropyl)sulfane

5-cyclopropyl-6-[(4-methoxy benzyl)oxy]pyridine-2-carbaldehyde

→

{5-cyclopropyl-6-[(4-methoxybenzyl)oxy]pyridin-2-yl}[4-(cyclopropylsulfanyl)phenyl]methanol

Ausbeute 73.5%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at −78° C. for 4.5 hours
2. 2
   workup.STIRRINGThe reaction solution was stirred in an ice bath
3. 3
   Extraktionfollowed by extraction with chloroform
4. 4
   TrocknenThe organic layer was dried over anhydrous magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   EinengenThe filtrate was concentrated under reduced pressure
7. 7
   SonstigeThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5→62:38)

Vorschrift

A solution of (4-bromophenyl)(cyclopropyl)sulfane (440 mg) in tetrahydrofuran (10 mL) was cooled to −78° C., and n-butyllithium (2.6 M, 0.74 mL) was slowly added dropwise, followed by stirring for 30 minutes. A solution of 5-cyclopropyl-6-[(4-methoxy benzyl)oxy]pyridine-2-carbaldehyde (417 mg) in tetrahydrofuran (5 mL) was slowly added dropwise, and the mixture was stirred at −78° C. for 4.5 hours. The reaction solution was stirred in an ice bath and a saturated ammonium chloride solution was added, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5→62:38) to give {5-cyclopropyl-6-[(4-methoxybenzyl)oxy]pyridin-2-yl}[4-(cyclopropylsulfanyl)phenyl]methanol as a yellow oil (469 mg, 73%).

Quelle