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

HRID 1193038노트

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HRID 1193038 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-152421b166b0419bb7930cdcbb2cb909
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680339B2

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