Dicyclohexylcarbodiimide → HCID 86604821, compound

Participants

Reaction Steps

In a 200 mL flask, 5 (7.63 g, 23.3 mmol), DCC (4.81 g, 23.3 mmol), 4-iodobenzoic acid (5.79 g, 23.3 mmol), and dimethylamino pyridine (0.85 g, 7.0 mmol) were dissolved in tetrahydrofuran (20 vol., 150 mL, freshly distilled from sodium and benzophenone) at room temperature and stirred overnight under Ar. The reaction mixture was filtered and the filtrate was added to a separatory funnel containing ether and water. The ether layer was rinsed several times with water, followed by dilute K2CO3, and then with dilute aqueous brine. The organic layer was evaporated onto silica gel and subsequently purified on silica gel with 3:1 hexane:ethyl acetate. Product 6A was a red viscous liquid (100% trans).

Provenance & Evidence