Lithium diisopropylamide → 2-(4-Benzyloxy-2,6-dimethylphenyl)-3-methoxy-5-[1-(tetrahydropyran-4-yl)-methylidene]cyclopent-2-enone

HRID 1193038ノート

反応式

HRID 1193038 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[C:17](=[O:23])[CH2:18][CH2:19][C:20]=2[O:21][CH3:22])=[C:11]([CH3:24])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N-]C(C)C)(C)C.[Li+].[O:33]1[CH2:38][CH2:37][CH:36]([CH:39]=O)[CH2:35][CH2:34]1.CC(C)([O-])C.[K+]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[C:17](=[O:23])[C:18](=[CH:39][CH:36]3[CH2:37][CH2:38][O:33][CH2:34][CH2:35]3)[CH2:19][C:20]=2[O:21][CH3:22])=[C:11]([CH3:24])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 2724682Lithium diisopropylamideHCID 9964078Tetrahydro-2H-pyran-4-carboxaldehydeHCID 23665647Potassium tert-butoxideHCID 580708252-(4-Benzyloxy-2,6-dimethylphenyl)-3-methoxycyclopent-2-enone

生成物 1

HCID 667096072-(4-Benzyloxy-2,6-dimethylphenyl)-3-methoxy-5-[1-(tetrahydropyran-4-yl)-methylidene]cyclopent-2-enone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 2-(4-benzyloxy-2,6-dimethylphenyl)-3-methoxycyclopent-2-enone (1.93 g, 6.0 mmol) in THF (25 ml) under a nitrogen atmosphere at −78° C. is added a solution of lithium diisopropylamide (3.33 ml, 6.0 mmol, 1.8M in tetrahydrofuran) dropwise over 1 minute. The reaction is then stirred at −78° C. for 30 minutes followed by the addition of 4-tetrahydropyran carbaldehyde (0.684 g, 6.0 mmol) in one portion. After a further 5 minutes at −78° C. the reaction is allowed to warm to ambient temperature and stir for an additional 1 hour. Potassium tert-butoxide (1.10 g, 9.82 mmol) is then added in one portion and the reaction mixture is allowed to stir for a further 1 hour at room temperature. After quenching with saturated ammonium chloride solution (50 ml) the crude product is extracted into ethyl acetate (50 ml), and the organic phase is dried over anhydrous magnesium sulfate and concentrated in vacuo. Purification by flash column chromatography affords 2-(4-benzyloxy-2,6-dimethylphenyl)-3-methoxy-5-[1-(tetrahydropyran-4-yl)-methylidene]cyclopent-2-enone as a white solid.

後処理

  1. waitAfter a further 5 minutes at −78° C. the reaction is allowed
  2. temperatureto warm to ambient temperature
  3. stirringstir for an additional 1 hour
  4. stirringto stir for a further 1 hour at room temperature
  5. customAfter quenching with saturated ammonium chloride solution (50 ml) the crude product
  6. extractionis extracted into ethyl acetate (50 ml)
  7. dry with materialthe organic phase is dried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customPurification by flash column chromatography

出典と根拠

ORDレコード
ord-152421b166b0419bb7930cdcbb2cb909
出典データセット
uspto-grants-2014_03
特許番号
US08680339B2

反応ノート

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