4-Chloro-2-methoxybenzaldehyde → 1-(4-Chloro-2-methoxyphenyl)propan-1-one

HRID 272693

反応式

HRID 272693 の反応式
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([O:10][CH3:11])[CH:3]=1.[CH3:12][CH2:13][Mg+].[Br-].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C1COCC1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6](=[O:7])[CH2:12][CH3:13])=[C:4]([O:10][CH3:11])[CH:3]=1

参加物

5

反応物 3

HCID 138651154-Chloro-2-methoxybenzaldehydeHCID 178418287HCID 178418287、化合物HCID 178461630HCID 178461630、化合物

生成物 1

HCID 199011951-(4-Chloro-2-methoxyphenyl)propan-1-one収率 66.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

4-Chloro-2-methoxy-benzaldehyde (0.54 g, 3.2 mmol) in 10 mL of THF was treated with 3.0 M EtMgBr (2 mL, 6.0 mmol) at room temperature. The solution was stirred for 1 hour and quenched with MeOH. The solution was poured into water, treated 10 mL of 10% HCl, extracted with EtOAc several times. The combined organic layers were washed brine, dried (MgSO4), filtered, and concentrated. The residue was diluted with CH2Cl2, treated with PCC (1.33 g, 6.4 mmol) for 2 hours. The reaction mixture was filtered through a pack of silica gel to give 0.42 g of the title compound. MS (DCI) m/e 199 (M+H)+.

後処理

  1. customquenched with MeOH
  2. additionThe solution was poured into water
  3. additiontreated 10 mL of 10% HCl
  4. extractionextracted with EtOAc several times
  5. washThe combined organic layers were washed brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. additionThe residue was diluted with CH2Cl2
  10. filtrationThe reaction mixture was filtered through a pack of silica gel

出典と根拠

ORDレコード
ord-255ec494d5f245e1888e65ce9141fd9c
出典データセット
uspto-grants-2008_11
特許番号
US07456169B2

関連ノート

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