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

HRID 630585

反応式

HRID 630585 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 1317354106-(n-Octyl)-6-phenylfulvene収率 72.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-68d668250d124f748eaba0f40d87d326
出典データセット
uspto-grants-2016_04
特許番号
US09315602B2

関連ノート

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