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

HRID 2104289

반응식

HRID 2104289 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-27b16a5324d146ce930e6c91a66a2252
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576239B2

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