Tetrahydrofuran → HCID 54735985, Verbindung

Reaktionsgleichung

[H-].[Na+].C[O:4][C:5]1[C:6](=[CH:13][CH:14]=[CH:15][C:16]=1[Cl:17])[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[O:10].C1C[O:21]CC1>>[C:9]([C:8]1[O:4][C:5]2[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:6]=2[C:7]=1[OH:21])([O:11][CH3:12])=[O:10]

Komponenten

Edukt 3

HCID 8028Tetrahydrofuran3×

HCID 24758Sodium hydride

HCID 53641489HCID 53641489, Verbindung

Produkt 1

HCID 54735985HCID 54735985, VerbindungAusbeute 80 %

Versuchsvorschrift

According to the procedure of D. C. Schroeder, et al., J. Org. Chem., 27, 586 (1962) to a stirred suspension of NaH (50% dispersion in mineral oil, washed with hexane) (4.5 g, 0.093 mol) in THF (20 mL) was added a solution of methyl (methyl 3-chlorosalicylyl)acetate (24.1 g, 0.093 mol) in THF (50 mL). Additional THF (60 mL) was added. After 1 hour, the mixture was heated under reflux for 1 hour, cooled, and partitioned between ether and H2O. The aqueous phase was acidified with 1N HCl and the precipitate was collected by filtration. This material was dissolved in ether. The solution was washed with H2O, dried (MgSO4), and concentrated to give a yellow solid (16.9 g, 80%).