Water → HCID 22626917, compound

Participants

Reaction Conditions

Reaction Steps

Compound 9 was dissolved in acetone (EMCO), at 60° C. in a 1 L, 1-neck round bottom flask. Pre-washed Amberlite IR-120 resin (Aldrich) was added with the water and the mixture was stirred at 60° C. for 40 minutes; aliquots were removed at 20 min (MCLS0995-078-1) and 40 min. HPLC analysis of the aliquots revealed that the de-protection of the aldehyde was complete in 20 minutes. The mixture was removed from the heating bath, filtered, and concentrated to ca. 40% of the initial volume under rotary evaporation (removal of acetone). The resulting aqueous suspension was partitioned between CH2Cl2 and sat. aq. sodium bicarbonate. The aqueous layer was extracted 2×CH2Cl2. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford product 10 (4.20 g, 81% yield).

Provenance & Evidence