Water → HCID 21999530, compound

Participants

Reaction Steps

Methoxyethoxymethyl chloride (150 mg, 1.2 mmol) is added to a solution of Compound 47 in 10 mL dry CH2Cl2 at 20° C. The reaction mixture is stirred for 1 hour and poured into 50 mL water. The product is extracted with diethyl ether (30 mL×2) and ethyl acetate (30 mL). The combined organic extracts are washed with 5% citric acid solution (50 mL), and brine (30 mL), dried over anhydrous magnesium sulfate and concentrated in vacuo to yield 425 mg yellow oil. The crude oil is then recrystallized from isopropyl alcohol to yield 240 mg (51%) of Compound 48 as a colorless solid. 1H-NMR (d6-DMSO) 5.48 (s, 2H); 4.36 (s, 3H); 3.99 (t, J=Hz, 2H); 3.58 (t, J=Hz, 2H); 3.36 (s, 3H). 19F-NMR (d6-DMSO) 142.90 (d, J=12.7, 1F); 142.97 (d, J=12.4 Hz, 1F); 153.12 (d, J=13.5 Hz, 1F); 155.54 (d, J=19.7 Hz, 1F); 155.82 (d, J=11.3 Hz, 1F); 157.13 (d, J=19.5 Hz, 1F).

Provenance & Evidence