反应详情

To the above dimethoxy amide 15 (117 mg, 0.22 mmol) in CH2Cl2 (1 ml) at 0° C. was added, under argon, 1.0 M 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, unter 0.063 mm, 30 g). Elution with a 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 16 with x=10) (34 mg, 31%), colorless oil, IR υmax (neat) 3300, 1600 cm-1 ; UV λmax (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 (8, m, H--Ar) ppm; MS m/e=493 (M+). ##STR23##

1. extractionextracted with ether (3x)
2. washThe organic solution was washed with water
3. customdried on magnesium sulfate
4. customevaporated to dryness
5. customThe residue was purified by "Flash chromatography" on silica gel (Kieselgel 60, Merck, unter 0.063 mm, 30 g)
6. washElution
7. additionwith a mixture of hexane-ethyl acetate (4:1 v/v)