Water → HCID 69516615, compound

Participants

Reaction Steps

To a solution of ethyl 8-chloro-6-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate prepared as in Example 17a, Step 3 (1.00 g, 3.10 mmole) in anhydrous DMF (10.0 mL) was added KI (51.5 mg, (0.310 mmole), K2CO3 (1.29 g, 9.30 mmole) and benzyl bromide (1.11 ml, 9.30 mmole). The suspension was stirred at room temperature for 2 h and poured into H2O (150 mL) and extracted with EtOAc (3×100 mL). The combined extracts were washed with brine (2×100 mL), dried over MgSO4 and concentrated in vacuo to give a yellow oil. Purification by silica chromatography (6:1 hexanes:EtOAc) gave 1.12 g (87.5% yield) of the product as a yellow crystalline solid: EIHRMS m/z 412.0689 (M+, C20H16ClF3O4, Calc'd 412.0680).

Provenance & Evidence