Tetrahydrofuran → HCID 71281816, compound

Reaction equation

Cl[C:2]1[N:17]=[CH:16][C:15]([I:18])=[C:14](Cl)[C:3]=1[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].[Na].[CH2:21]1[CH2:25][O:24][CH2:23][CH2:22]1>>[CH2:23]([O:24][C:2]1[N:17]=[CH:16][C:15]([I:18])=[C:14]([O:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]=1[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5])[C:22]1[CH:21]=[CH:25][CH:2]=[CH:3][CH:4]=1

Participants

Reactant 3

HCID 8028Tetrahydrofuran2×

HCID 5360545Sodium

HCID 89421783HCID 89421783, compound

Product 1

HCID 71281816HCID 71281816, compoundYield 51%

Procedure

Into a solution of benzyl 2,4-dichloro-5-iodonicotinate (3.7 g, 9.1 mmol) in THF (20 mL) was added a solution of sodium benzoxide in THF (1.0 M×20 mL, 20 mmol). The mixture was stirred at room temperature overnight. The reaction was quenched with saturated NH4Cl. The mixture was extracted with ethyl acetate. The organic layers were combined and washed with brine, dried over sodium sulfate, evaporated and purified by silica chromatography (0-7% ethyl acetate in hexanes) to give benzyl 2,4-bis(benzyloxy)-5-iodonicotinate (2.55 g, 51%).