Water → HCID 53738029, compound

Participants

Reaction Steps

To the above dimethoxy amide 4, (117 mg, 0.22 mmol) in CH2Cl2 (1 ml) at 0° C. was added, under argon, 1.0M borane tribromide (675 μl). The solution was stirred for 1 hour, then poured into water and extracted with ether (3x). The organic solution was washed with water, dried on magnesium sulfate, and evaporated to dryness. The residue was purified by "Flash chromatography" on silica gel (Kieselgel 60, Merck, under 0.063 mm, 30 g). Elution with mixture of hexane-ethyl acetate (4:1 v/v) gave N-butyl, N-methyl-12,13-Bis (4-hydroxyphenyl)-12-pentadecenoic amide (EM-142, compound 5 with x=10) (34 mg, 31%), colorless oil, IR vmax (neat) 3300, 1600 cm-1 ; UV γmax (log ε)=235 (4.25) nm; 1H-NMR (δ, CDCl3), 0.76 (3H, t, J=7.3 Hz, --CH2CH3 ), 0.96 (3H, t, J=7.3 Hz, N (CH2)3CH3 ), 2.05-2.20 (4H, m, CH2 --C=C--CH2 --), 2.35 (2H, t, J=7.0 Hz, --CH2CON--), 2.97 and 3.00 (3H, s, --NCH3 ), 3.29 and 3.41 (2H, 2t, J=7.3 Hz, --N--CH2 --), and 6.59-7.09 (8H, m, H--Ar) ppm; MS m/e=493 (M+). ##STR49##

Provenance & Evidence