Sodium, 2,4-cyclopentadien-1-yl- → 6-(n-Octyl)-6-phenylfulvene

HRID 630585

반응식

HRID 630585 반응식
[C:1]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[CH-:17]1[CH:21]=[CH:20][CH:19]=[CH:18]1.[Na+]>C1COCC1>[CH2:2]([C:1]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[C:20]1[CH:19]=[CH:18][CH:17]=[CH:21]1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

참가 물질

4

반응물 2

HCID 78681Sodium, 2,4-cyclopentadien-1-yl-HCID 801081-Phenylnonan-1-one

생성물 1

HCID 1317354106-(n-Octyl)-6-phenylfulvene수율 72.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Under a nitrogen atmosphere, 2.0 g (9.2 mmol) of n-nonanophenone and 30 mL of dry THF were put into a 100-mL Schlenk flask to produce a solution. To this solution, 5.6 mL (11.2 mmol) of a solution of 2.0-M sodium cyclopentadienide in THF was added under cooling with ice, and the product was stirred at room temperature for 19 hours. Then, the obtained deep red solution was quenched with dilute aqueous hydrochloric acid under cooling with ice. Then, 30 mL of diethyl ether was added thereto, and the soluble part in diethyl ether was extracted, and the organic layer was neutralized and washed with an aqueous solution of saturated sodium hydrogen carbonate, water, and a saturated salt solution and then dehydrated with anhydrous magnesium sulfate. The solvent was distilled off, and then the residue was purified by silica gel column chromatography to obtain an objective that was a red liquid (amount: 1.77 g and yield: 72.5%).

후처리

  1. customto produce a solution
  2. temperatureunder cooling with ice
  3. customThen, the obtained deep red solution was quenched with dilute aqueous hydrochloric acid
  4. temperatureunder cooling with ice
  5. additionThen, 30 mL of diethyl ether was added
  6. extractionthe soluble part in diethyl ether was extracted
  7. washwashed with an aqueous solution of saturated sodium hydrogen carbonate, water
  8. distillationThe solvent was distilled off
  9. customthe residue was purified by silica gel column chromatography
  10. customto obtain an objective that

출처 및 근거

ORD 기록
ord-68d668250d124f748eaba0f40d87d326
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315602B2

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