Formic Acid → Methyl 4-oxoadamantane-1-carboxylate

反応式

S(=O)(=O)(O)O.O[C:7]12[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([C:10]3=[O:17])[CH2:8]1)[CH2:14]2.[CH3:18]O.[CH:20]([OH:22])=[O:21]>>[CH3:18][O:21][C:20]([C:7]12[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([C:10]3=[O:17])[CH2:8]1)[CH2:14]2)=[O:22]

参加物

反応物 4

HCID 284Formic Acid2 回

HCID 887Methanol

HCID 1118Sulfuric Acid

HCID 64184Idramantone

生成物 1

HCID 4078246Methyl 4-oxoadamantane-1-carboxylate

反応条件

温度: 60 °C

実験手順

38 mL of fuming sulfuric acid were placed in a two necked flask and warmed to 60° C. 1.5 g of 5-hydroxy-2-adamantanone, dissolved in formic acid (8.5 ml) were added dropwise over the course of 2 h. Another 9 mL of formic acid were added over a period of 2 h and stirring was continued at 60° C. for 1 h and at room temperature overnight. Under ice cooling, the reaction mixture was poured on 100 mL of dry methanol, stirred at room temperature for 2 h and subsequently poured onto 400 mL of ice. The aqueous layer was extracted with dichloromethane three times, the combined organic layer was dried over sodium sulphate and evaporated to dryness to give 1.64 g of the desired product. Rt=1.75 min (5). Detected mass: 209.2 (M+H+).