Sodium Acetate → HCID 57845616, compound

Participants

Reaction Steps

A solution of 690 mg (1.72 mmol) of alcohol 4 in 4 mL of dichloromethane was added via pipette to a mixture of PCC (650 mg, 3.0 mmol), sodium acetate (325 mg, 3.96 mmol), and Celite (1.23 g) in 7 mL of DCM. The pipette was rinsed with an additional 3 mL of DCM to complete the transfer. The mixture was stirred sealed at 25° C. for 3 h. The mixture was worked up by filtration through 25 g of silica gel and washed with 200 mL of 1:4 EA:hexanes. The filtrate was concentrated in vacuo to yield 500 mg (72% yield) of crude aldehyde 5 as an oil; 1H NMR (CDCl3): 1.45-1.85 (m, 10H), 2.04-3.00 (m, 10H), 3.51 (m, 1H), 3.81 (m, 1H), 4.07 (m, 1H), 4.59 (m, 4H), 5.26 (m, 1H), 5.45 (m, 1H), 5.92 (m, 1H), 9.75 (dd, J=2.1, 9 Hz, 1H).

Provenance & Evidence