Methyl 3-chlorobenzoate → HCID 178520885、化合物

HRID 2369819

反応式

HRID 2369819 の反応式
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9]C)=O.[OH:14][C:15]1[CH:25]=[CH:24][C:18]([CH:19]=[CH:20][C:21](=[O:23])[CH3:22])=[CH:17][CH:16]=1>CN(C=O)C>[Cl:3][C:4]1[CH:5]=[C:6]([C:7](=[O:9])/[CH:22]=[C:21](\[OH:23])/[CH:20]=[CH:19]/[C:18]2[CH:17]=[CH:16][C:15]([OH:14])=[CH:25][CH:24]=2)[CH:11]=[CH:12][CH:13]=1

参加物

5

反応物 3

HCID 17946Methyl 3-chlorobenzoateHCID 24758Sodium hydrideHCID 956483-Buten-2-one, 4-(4-hydroxyphenyl)-

生成物 1

HCID 178520885HCID 178520885、化合物収率 60.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

NaH (60% dispersion, 0.477 g, 11.9 mmol) was added to a solution of methyl 3-chlorobenzoate (0.677 g, 3.97 mmol) and 4-hydroxybenzylideneacetone (0.644 g, 3.97 mmol) in anhydrous DMF (20 mL) at 0° C. The reaction was allowed to warm to room temperature overnight and quenched with saturated aqueous NH4Cl and neutralized with 1M HCl. The reaction was diluted with ethyl acetate (80 mL) and the organic layer washed successively with saturated aqueous NaHCO3 and brine. The organic phase was separated and dried over Na2SO4, filtered, and concentrated in vacuo to provide the condensation product as a yellow oil (0.717 g, 60% yield).

後処理

  1. customquenched with saturated aqueous NH4Cl and neutralized with 1M HCl
  2. additionThe reaction was diluted with ethyl acetate (80 mL)
  3. washthe organic layer washed successively with saturated aqueous NaHCO3 and brine
  4. customThe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-ef039adaaca1415fbcdad925a1ad98d3
出典データセット
uspto-grants-2014_04
特許番号
US08710038B2

関連ノート

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