Sodium Acetate → HCID 57814789, compound

Participants

Reaction Steps

A solution of 700 mg (1.73 mmol) of alcohol 11 in 4 mL of dichloromethane was added via pipette to a mixture of PCC (700 mg, 3.23 mmol), sodium acetate (350 mg, 4.26 mmol), and Celite (1.3 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 30° C. for 1.5 h. The mixture was worked up by filtration through 20 g of silica gel and washed with 200 mL of 1:4 EA:hexanes. The filtrate was concentrated in vacuo to yield 500 mg) of crude aldehyde 12. Further FCC purification on 10 g of silica gel yielded 380 mg of purified aldehyde 12 (54% yield) as an oil; 1H NMR (CDCl3); 0.93 (t, J=7.2 Hz, 3H), 1.31 (m, 10H), 1.42-1.90 (m, 17H), 1.94-2.44 (m, 4H), 2.28 (t, J=7.5 Hz, 2H), 2.52 (m, 1H), 2.68 (m, 1H), 3.48 (m, 2H), 3.81 (m, 2H), 4.01 (t, J=6.6 Hz, 3H), 4.06 (m, 1H), 4.5-4.64 (m, 2H), 9.75 (m, J=2.1, 9 Hz, 1H).

Provenance & Evidence