Methyl acetoacetate → HCID 58762397, 화합물

HRID 858861

반응식

HRID 858861 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 58762397HCID 58762397, 화합물수율 48.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ec9771eb0d7143eb93ac6a42f99719c9
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07148226B2

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