Cyclohexylfulvene → (1-Methyl-1-cyclohexyl)cyclopentadiene

HRID 270987노트

반응식

HRID 270987 반응식
[CH:1]1([C:7]2[C:11](=C)[CH:10]=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:13][Li]>C1COCC1.CCOCC.O>[CH3:13][C:1]1([C:7]2[CH2:11][CH:10]=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

참가 물질

6

반응물 2

HCID 22327799CyclohexylfulveneHCID 178418348HCID 178418348, 화합물

생성물 1

HCID 14688277(1-Methyl-1-cyclohexyl)cyclopentadiene수율 38%

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매2회HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 6.50 g (44.5 mmol) of cyclohexylfulvene in 60 ml of THF, 44.8 ml (51.1 mmol) of an ether solution of methyllithium was dropwise added in a nitrogen atmosphere with ice cooling, followed by stirring at room temperature for one night. After the reaction solution was diluted with 100 ml of ether, 30 ml of water was added. The separated organic phase was washed with water and a saturated saline solution, then dried over magnesium sulfate and filtered. From the filtrate, the solvent was removed under reduced pressure to obtain a liquid. The liquid was isolated and purified by column chromatography (silica gel, developing solvent: hexane) to obtain 2.72 g (16.76 mmol) of a colorless transparent liquid (yield: 38%) The analyzed values are given below.

후처리

  1. additionwas added
  2. washThe separated organic phase was washed with water
  3. dry with materiala saturated saline solution, then dried over magnesium sulfate
  4. filtrationfiltered
  5. customFrom the filtrate, the solvent was removed under reduced pressure
  6. customto obtain a liquid
  7. customThe liquid was isolated
  8. custompurified by column chromatography (silica gel, developing solvent: hexane)

출처 및 근거

ORD 기록
ord-f30bcdc8296743108352e821da840924
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449533B2

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