3-Chloro-1,1-diethoxypropane → HCID 71294611, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the diol (6Z,9Z,29Z,32Z)-19-((8Z,11Z)-heptadeca-8,11-dien-1-yl)octatriaconta-6,9,29,32-tetraene-18,20-diol (11) (832 mg, 1.05 mmol) and 3-chloropropionaldehyde diethylacetal (351 μL, 2.10 mmol) in toluene (10 mL) was treated with PPTS (100 mg) and heated (80° C., 2 h). After cooling (rt) the reaction mixture was poured into sat. aq. NaHCO3, extracted with EtOAc, washed with brine, dried (Na2SO4), filtered and concentrated. The crude product was dissolved in a solution of (CH3)2NH (15 mL, 5.6M in EtOH), treated with tetrabutylammonium iodide (25 mg), transferred to a sealed reaction vessel and heated (80° C., 20 h). Once complete the yellow solution was concentrated and the residue was subjected to chromatography (100% EtOAc) to yield 2-(4,5-di((8Z,11Z)-heptadeca-8,11-dien-1-yl)-6-((9Z,12Z)-octadeca-9,12-dien-1-yl)-1,3-dioxan-2-yl)-N,N-dimethylethanamine (12) (203 mg, 22% over 2 steps) as a pale yellow oil. Rf 0.41 (8% CH3OH—CHCl3); 1H NMR (400 MHz, CDCl3) 5.43-5.29 (m, 12H), 4.88-4.83 (m, 0.5H), 4.64-4.58 (m, 0.5H), 3.89-3.82 (m, 0.5H), 3.56-3.50 (m, 1H), 3.35-3.27 (m, 0.5H), 2.78 (app. t, 6H), 2.65-2.50 (m, 2H), 2.46-2.31 (m, 6H), 2.11-2.03 (m, 12H), 1.92-1.78 (m, 2H), 1.65-1.11 (m, 57H), 0.90 (t, 9H). FW 876.51, C60H109NO2.

Provenance & Evidence