Ethyl Acetate → 4-(4-Chlorophenyl)-3-cyano-3-phenyl-2-butanone

HRID 2104289

反応式

HRID 2104289 の反応式
[C:1]([CH:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:5]#[N:6])(=[O:3])[CH3:2].[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>C(#N)C.O>[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][C:4]([C:5]#[N:6])([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:1](=[O:3])[CH3:2])=[CH:16][CH:15]=1

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 20547Alpha-phenylacetoacetonitrileHCID 693291-(Bromomethyl)-4-chlorobenzene

生成物 1

HCID 664309254-(4-Chlorophenyl)-3-cyano-3-phenyl-2-butanone

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

To a solution of α-acetylphenylacetonitrile (1.0 g, 6.3 mmol) in acetonitrile (25 mL) was added 4-chlorobenzyl bromide (1.3 g, 6.3 mmol) and cesium carbonate (8.2 g, 25 mmol). After stirring at room temperature for 2 h, the reaction mixture was poured into ethyl acetate (100 mL) and water (100 mL). The organic layer was separated, washed with brine, dried over magnesium sulfate, filtered, and concentrated to dryness, and the residue was purified on a silica gel column eluting with 1 to 5% ethyl acetate in hexane to give the title compound. 1H NMR (400 MHz, CD3OD): δ 7.5-6.9 (m, 9H), 3.56 (d, 1H), 3.37 (d, 1H), 2.22 (s, 3H). LC-MS: m/e 306 (M+Na)+ (3.0 min).

後処理

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customthe residue was purified on a silica gel column
  7. washeluting with 1 to 5% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-27b16a5324d146ce930e6c91a66a2252
出典データセット
uspto-grants-2009_08
特許番号
US07576239B2

関連ノート

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