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

HRID 508589

反応式

HRID 508589 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒2 回HCID 8058Hexane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d8754dd88e3f4ae7b1731c73c8e7904b
出典データセット
uspto-grants-2015_08
特許番号
US09096533B2

関連ノート

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