1,2-Dichloroethane → HCID 70006201, compound

Participants

Reaction Steps

Wang resin bound trans-7-[2-Oxo-5-(2-tributylstannanyl-vinyl)-cyclopentyl]-heptanoic acid. A dichloromethane (5 mL) solution of trans-7-[2-oxo-5-(2-tributylstannanyl-vinyl)-cyclopentyl]-heptanoic acid of Step E (6.35 g, 12.05 mmol, 3 eq) was added to the Wang resin (5.66 g, 4.02 mmol, 1 eq) along with diisopropylethylamine (6.23 g, 48.20 mmol, 12 eq). The mixture was allowed to swell for 1 hour, and EDC (2.31 g, 12.05 mmol, 3 eq) was added followed by 4-dimethylaminopyridine (catalytic amount about 20 mg). The mixture was stirred at room temperature overnight. The resin was filtered, washed with dichloromethane (20 mL×2), repeatedly swollen with dichloromethane (20 mL) and shrunk with methanol (20 mL). The resin was washed with diethyl ether (20 mL×3) and dried on a filter funnel attached to a water aspirator for 30 minutes. Further drying under high vacuum for 5 hours provided the title compound as a free-flowing yellow resin.

Provenance & Evidence