Tetrahydrofuran → 2-Bromo-9,9-dimethoxyethylfluorene

HRID 720019

반응식

HRID 720019 반응식
[Br:1][C:2]1C=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.[CH3:15][C:16]([CH3:19])([O-:18])C.[K+].S([O:25][CH2:26]COC)(=O)(=O)C.O1CCC[CH2:31]1>O>[Br:1][CH2:2][CH2:3][C:4]1[C:15]2[C:16]([O:25][CH3:26])([O:18][CH3:31])[C:19]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[CH:7]=[CH:6][CH:5]=1

참가 물질

6

반응물 4

HCID 8028Tetrahydrofuran2회HCID 143362-Bromo-9H-fluoreneHCID 1462932-Methoxyethyl methanesulfonateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 695870882-Bromo-9,9-dimethoxyethylfluorene

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a solution of 2-bromofluorene (2.45 g, 10 mmol) in tetrahydrofuran (dry, 75 ml) was added potassium t-butoxide (3.36 g, 30 mmol), giving a deep orange solution. The mixture was stirred at ambient temperature for 10 min and added 2-methoxyethyl mesylate in tetrahydrofuran dropwise. Exothermic reaction was observed. Stirring was continued at ambient temperature for overnight to give an orange solution. At the end of the reaction, it was diluted with water (150 ml). The products extracted with ethylacetate (30 ml) and washed with water. Organic layer was dried over magnesium sulfate and concentrated in vacuuo to afford the crude product. It was purified by preparative thin layer chromatography (silica gel, Rf=0.3 using hexane-EtOAc/3:2 as eluent) to give 2-bromo-9,9-dimethoxyethylfluorene (3.3 g).

후처리

  1. customgiving a deep orange solution
  2. customExothermic reaction
  3. stirringStirring
  4. waitwas continued at ambient temperature for overnight
  5. customto give an orange solution
  6. customAt the end of the reaction, it
  7. extractionThe products extracted with ethylacetate (30 ml)
  8. washwashed with water
  9. dry with materialOrganic layer was dried over magnesium sulfate
  10. concentrationconcentrated in vacuuo
  11. customto afford the crude product
  12. customIt was purified by preparative thin layer chromatography (silica gel, Rf=0.3 using hexane-EtOAc/3:2 as eluent)

출처 및 근거

ORD 기록
ord-67040ca6b49542a6ac6a7c0f8ef870c1
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07132572B2

연결된 노트

불러오는 중…