Formic Acid → Methyl 4-oxoadamantane-1-carboxylate

HRID 38450

반응식

HRID 38450 반응식
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]

참가 물질

5

반응물 4

HCID 284Formic Acid2회HCID 887MethanolHCID 1118Sulfuric AcidHCID 64184Idramantone

생성물 1

HCID 4078246Methyl 4-oxoadamantane-1-carboxylate

반응 조건

온도
60 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-69184de00b8441799389a03a749f14b9
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524737B2

연결된 노트

불러오는 중…