Potassium Carbonate → 3-Benzyl-2-cyclopentenol

HRID 1934321ノート

反応式

HRID 1934321 の反応式
[CH2:1]([C:8]1[CH2:12][CH2:11][C:10](=[O:13])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O-])([O-])=O.[K+].[K+]>CCOCC>[CH2:1]([C:8]1[CH2:12][CH2:11][CH:10]([OH:13])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 118299173-Benzylcyclopent-2-en-1-oneHCID 21226445Aluminium lithium hydride

生成物 1

HCID 121097083-Benzyl-2-cyclopentenol収率 95.7%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

A solution of compound 3-benzyl-2-cyclopenten-1-one (3.1 g, 18 mmol) in ether (100 mL) was slowly added to a suspension of lithium aluminum hydride (LAH) (684 mg, 0.87 mol) and ether (100 mL) at 0° C. under N2. The resulting mixture was stirred overnight at ambient temperature and cooled to 0° C. Saturated K2CO3 solution was added to quench the excess LAH, the mixture was filtered through Celite and washed with several portions of ether. The combined organic layers were dried (MgSO4) and concentrated in vacuo to give compound the title compound (3 g, 94%) as a colorless oil. NMR(CDCl3):3.41 (ABq, J=6 Hz, 2H, benzylic protons), 4.80 (bs, 1H, CHOH), 5.22 (bs, 1H, olefinic proton), 7.22 (m, 5H, aromatic protons).

後処理

  1. temperaturecooled to 0° C
  2. customto quench the excess LAH
  3. filtrationthe mixture was filtered through Celite
  4. washwashed with several portions of ether
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-15544be88820430e968d7a3092ee7cde
出典データセット
uspto-grants-2002_05
特許番号
US06384031B1

反応ノート

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