Hydrochloric Acid → Benzene, 1-cyclopenten-1-yl-

HRID 474248ノート

反応式

HRID 474248 の反応式
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCOCC.[C:14]1(=O)[CH2:18][CH2:17][CH2:16][CH2:15]1.Cl>C1COCC1>[C:14]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:18][CH2:17][CH2:16][CH:15]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 8452CyclopentanoneHCID 178418255HCID 178418255、化合物

生成物 1

HCID 136652Benzene, 1-cyclopenten-1-yl-収率 100%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 3.0 M solution of phenylmagnesium bromide in ether (49.7 mL, 149 mmol) was added THF (300 mL). To this solution cooled to 0° C. cyclopentanone (13.23 mL, 149 mmol) was added. The reaction mixture was stirred at room temperature for 30 min, then at reflux for 2 h. Ice (20 g) was added, followed by 6 N HCl, until the precipitate dissolved. The product was extracted with ether. The combined etherial layers were washed with saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate and filtered. The solvent was removed in vacuo and the residue was purified by column chromatography on silica gel to give cyclopentenylbenzene (21.49 g, 149 mmol, 100% yield) as a colorless oil. LC-MS (M+H)+=145.1. 1H NMR (500 MHz, chloroform-d) δ ppm 7.48 (2H, d, J=7.3 Hz), 7.35 (2H, t, J=7.8 Hz), 7.22-7.27 (1H, m), 6.22 (1H, t, J=2.1 Hz), 2.70-2.80 (2H, m), 2.52-2.64 (2H, m), 2.01-2.12 (2H, m).

後処理

  1. additionwas added
  2. temperatureat reflux for 2 h
  3. dissolutiondissolved
  4. extractionThe product was extracted with ether
  5. washThe combined etherial layers were washed with saturated sodium bicarbonate solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe solvent was removed in vacuo
  9. customthe residue was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-7dd1daa45bab4f48af1acd4a231361a0
出典データセット
uspto-grants-2014_01
特許番号
US08637523B2

反応ノート

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