Ethyl Acetate → Ethyl 2-[2-(2,6-diethyl-4-methylphenylacetyl)-2-methylhydrazono]propanoate

HRID 508594

반응식

HRID 508594 반응식
C(=O)([O-])[O-].[K+].[K+].[CH3:7][NH:8][N:9]=[C:10]([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12].[CH2:17]([C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH2:26][CH3:27])[C:20]=1[CH2:28][C:29](Cl)=[O:30])[CH3:18].C(OCC)(=O)C>C(#N)C.CCCCCC>[CH2:17]([C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH2:26][CH3:27])[C:20]=1[CH2:28][C:29]([N:8]([CH3:7])[N:9]=[C:10]([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:30])[CH3:18]

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 574373202,6-Diethyl-4-methylphenylacetyl chlorideHCID 73828661Ethyl 2-(methylhydrazono)propanoate

생성물 1

HCID 76550641Ethyl 2-[2-(2,6-diethyl-4-methylphenylacetyl)-2-methylhydrazono]propanoate수율 49.4%

시약·촉매·용매 2

HCID 6342Acetonitrile용매2회HCID 8058Hexane용매

실험 절차

1.5 g of potassium carbonate was added to a solution of 2.0 g of ethyl 2-(methylhydrazono)propanoate in 35 mL of acetonitrile. The mixture was stirred under cooling with ice, to which a solution of 2.6 g of 2,6-diethyl-4-methylphenylacetyl chloride in 10 mL of acetonitrile was added dropwise over about 20 minutes. The resulting mixture was further stirred for 3.5 hours at room temperature, and then concentrated under reduced pressure. To the residue obtained was added 20 mL of ice-water, which was extracted with ethyl acetate (20 mL×3). The extracts were combined, washed with a saturated sodium chloride aqueous solution (20 mL×2), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained was subjected to basic alumina column chromatography (ethyl acetate:hexane=1:3 as eluent) to yield 1.9 g of the title compound as white crystals.

후처리

  1. additionwas added dropwise over about 20 minutes
  2. stirringThe resulting mixture was further stirred for 3.5 hours at room temperature
  3. concentrationconcentrated under reduced pressure
  4. customTo the residue obtained
  5. extractionwas extracted with ethyl acetate (20 mL×3)
  6. washwashed with a saturated sodium chloride aqueous solution (20 mL×2)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue obtained

출처 및 근거

ORD 기록
ord-d82cc636d9dc4fab9d720635e3408283
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096534B2

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