Iodine → HCID 67504868, compound

Participants

Reaction Conditions

Reaction Steps

Mg (10.6 g, 438 mmol) was dispersed in THF (160 mL) and 1 crystal of I2 and 1,2-dibromoethane (0.25 mL) were added. 4-Chlorotetrahydro-2H-pyran, dissolved in THF (50 mL), was added dropwise and the mixture was heated at 70° C. for 1.5 h. The solution was cooled to 0° C. and the product from step A was added dropwise as a solution in toluene (100 mL). The reaction was aged at rt for 2 h and the mixture was filtered eluting with MTBE. The reaction was quenched with sat. NH4Cl (aq) and extracted twice with EtOAc. The organic layers were combined and washed with brine, dried with Na2SO4, filtered and concentrated. The resulting oil was purified by flash chromatography on silica gel gradient eluted with 100% EtOAc to 8% MeOH in EtOAc affording the desired slow eluting diastereomer, (B-1). HPLC/MS: 327.1 (M+1); Rt=231 min. The fast eluting isomer on silica gel (B-2) was also isolated. HPLC/MS: 327.1 (M+1); Rt=2.15 min

Provenance & Evidence