Acetone → HCID 57772123、化合物

反応式

[CH:1]1[C:5]2=[C:6](O)[C:7]3[CH:14]=[CH:13][C:11](=[O:12])[O:10][C:8]=3[CH:9]=[C:4]2[O:3][CH:2]=1.[C:16]([O-])([O-])=[O:17].[K+].[K+].[I-].[Na+].P(O)([O-])([O-])=[O:25].[Na+].[Na+].[CH3:31][C:32]([CH3:34])=[O:33]>>[CH3:16][O:17][C:31](=[O:25])[CH:32]([O:33][C:6]1[C:5]2[CH:1]=[CH:2][O:3][C:4]=2[CH:9]=[C:8]2[C:7]=1[CH:14]=[CH:13][C:11](=[O:12])[O:10]2)[CH3:34]

参加物

反応物 5

HCID 180Acetone

HCID 5238Sodium Iodide

HCID 11430Potassium Carbonate

HCID 24203Sodium Phosphate, Dibasic

HCID 5280371Bergaptol

生成物 1

HCID 57772123HCID 57772123、化合物収率 38.5%

実験手順

To a mixture of Bergaptol (10 grams, 49.5 mmol), anhydrous K2CO3 (20 grams, 144.7 mmol), Sodium iodide (2.4 grams, 16 mmol), disodium phosphate (2.4 grams, 17 mmol) in anhydrous acetone (250 mL) was added methyl 2-chloro propionate (10 mL, 87.7 mmol) and refluxed for 8 hours. Acetone was distilled and water (100 mL) was added. Crude 40 was filtered and recrystallized in a mixture of methanol:chloroform (9:1) to give pure 40 (5.5 grams, 38.5%) as a white powder. The melting point was found to be 149.6-151.6° C. The structure was confirmed with IR and NMR. IHNMR (CDCl3) δ 1.78(d, 3H,—CH3), 3.68(s, 3H, ester), 5.18(q, 1H, CH), 6.31(d, 1H, J=12.1 Hz, pyran), 6.84(d, 1H, J=1.1 Hz, furan), 7.22(s, 1H, Ar), 7.64(d, 1H, J=1.1 Hz, furan), 8.36(d, 1H, J=12.1 Hz, pyran).