Methyl acetoacetate → HCID 58762397、化合物

HRID 858861

反応式

HRID 858861 の反応式
[Li+].CC([N-]C(C)C)C.[C:9]([O:15][CH3:16])(=[O:14])[CH2:10][C:11]([CH3:13])=[O:12].[CH:17]1([C:22](=[O:36])[CH2:23][CH2:24][C:25]#[C:26][C:27]2[CH:32]=[C:31]([CH3:33])[C:30]([OH:34])=[CH:29][C:28]=2[CH3:35])[CH2:21][CH2:20][CH2:19][CH2:18]1>C1COCC1>[CH3:16][O:15][C:9](=[O:14])[CH2:10][C:11](=[O:12])[CH2:13][C:22]([CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)([OH:36])[CH2:23][CH2:24][C:25]#[C:26][C:27]1[CH:32]=[C:31]([CH3:33])[C:30]([OH:34])=[CH:29][C:28]=1[CH3:35]

参加物

5

反応物 3

HCID 7757Methyl acetoacetateHCID 2724682Lithium diisopropylamideHCID 587625021-Cyclopentyl-5-(4-hydroxy-2,5-dimethyl-phenyl)-pent-4-yn-1-one

生成物 1

HCID 58762397HCID 58762397、化合物収率 48.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a freshly prepared solution of LDA (1 M, 2.2 mL, 2.2 mmol) cooled to 0° C. was added methyl acetoacetate (0.12 mL, 1.1 mmol) dissolved in THF (1 mL). After stirring for 30 minutes, 1-cyclopentyl-5-(4-hydroxy-2,5-dimethyl-phenyl)-pent-4-yn-1-one (0.10 g, 0.37 mmol) from Step 1 above dissolved in THF (1 mL) was added. The reaction was stirred for 1 hour, and then warmed to room temperature. After quenching with 10 mL saturated ammonium chloride, the layers were separated. The aqueous layer was extracted with 2×15 mL CH2Cl2, and the organic layers were combined. After drying over Na2SO4, and filtering to remove the solids, the mother liquor was concentrated to an oil. Flash chromatography of the oil gave the desired product (69 mg, 48% yield).

後処理

  1. additionwas added
  2. stirringThe reaction was stirred for 1 hour
  3. customAfter quenching with 10 mL saturated ammonium chloride
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted with 2×15 mL CH2Cl2
  6. dry with materialAfter drying over Na2SO4
  7. filtrationfiltering
  8. customto remove the solids
  9. concentrationthe mother liquor was concentrated to an oil

出典と根拠

ORDレコード
ord-ec9771eb0d7143eb93ac6a42f99719c9
出典データセット
uspto-grants-2006_12
特許番号
US07148226B2

関連ノート

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