反应详情

温度

180 °C

In a microwave tube, (1R,10R,11S,16S)-3,5-dimethoxy-1,11,15,15-tetramethyl-8-oxatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene (Compound No. 38) (0.15 g, 0.42 mmol), Na2S (0.20 g, 2.6 mmol) and NMP (3 mL) were placed. The tube was sealed and subjected to microwave heating at 180° C. for 1 h. The reaction was cooled to room temperature, diluted with EtOAc (100 mL) and washed with water (50 mL). The organic layer was separated, dried (Na2SO4) and concentrated. Purification by column chromatography on silica gel (Hexanes/EtOAc, 4:1) gave (1R,10R,11S,16S)-5-methoxy-1,11,15,15-tetramethyl-8-oxatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-3-ol (Compound No. 39) (0.06 g, 43%) as a colourless solid. 1H NMR (CDCl3): δ 6.15 (d, 1H), 6.00 (d, 1H), 4.93 (s, 1H), 4.27 (m, 1H), 3.97 (t, 1H), 3.68 (s, 3H), 3.00 (m, 1H), 1.75-1.40 (m, 8H), 1.37 (s, 3H), 1.20-0.93 (m, 2H), 0.92 (s, 3H), 0.90 (m, 1H) 0.68 (s, 3H), 0.62 (s, 3H). MS m/z 345 (C22H32O3+H+).

1. customThe tube was sealed
2. temperatureThe reaction was cooled to room temperature
3. washwashed with water (50 mL)
4. customThe organic layer was separated
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated
7. customPurification by column chromatography on silica gel (Hexanes/EtOAc, 4:1)