Tetrahydrofuran → HCID 54735985, 화합물

반응식

[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]

참가 물질

반응물 3

HCID 8028Tetrahydrofuran3회

HCID 24758Sodium hydride

HCID 53641489HCID 53641489, 화합물

생성물 1

HCID 54735985HCID 54735985, 화합물수율 80%

실험 절차

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%).