Formic Acid → Methyl 4-oxoadamantane-1-carboxylate

HRID 38450

反応式

HRID 38450 の反応式
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

5

反応物 4

HCID 284Formic Acid2 回HCID 887MethanolHCID 1118Sulfuric AcidHCID 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+).

後処理

  1. additionwere added dropwise over the course of 2 h
  2. stirringstirred at room temperature for 2 h
  3. extractionThe aqueous layer was extracted with dichloromethane three times
  4. dry with materialthe combined organic layer was dried over sodium sulphate
  5. customevaporated to dryness

出典と根拠

ORDレコード
ord-69184de00b8441799389a03a749f14b9
出典データセット
uspto-grants-2013_09
特許番号
US08524737B2

関連ノート

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