Dimethyl Sulfoxide → HCID 12987276, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of oxalyl chloride (5.07 mmol) in CH2Cl2 (10 mL) at -60° C. is added DMSO (10.56 mmol) in CH2Cl2, dropwise under an argon atmosphere. The resulting mixture is stirred at -60° C. for 5 min, and a solution of 9-hydroxymethyl-9-phenylfluorene (4.4 mmol) in CH2Cl2 (2 mL) is then added dropwise over 10 minutes to the reaction mixture. The reaction mixture is allowed to stir at -50° C. for another 15 min after the addition is completed. Et3N (3 mL) is added dropwise and the resulting mixture allowed to warm to room temperature over 30 min. The reaction mixture is quenched with H2O (15 mL). The resulting mixture is extracted with CH2Cl2 (2×30 mL). The combined CH2Cl2 layers are washed with brine (1×30 mL), dried (Na2SO4) and concentrated in vacuo to afford the crude aldehyde.

Provenance & Evidence