Methyl 3-chlorobenzoate → HCID 178520885, 화합물

HRID 2369819

반응식

HRID 2369819 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 178520885HCID 178520885, 화합물수율 60.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ef039adaaca1415fbcdad925a1ad98d3
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08710038B2

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