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

HRID 272693

반응식

HRID 272693 반응식
[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

참가 물질

5

반응물 3

HCID 138651154-Chloro-2-methoxybenzaldehydeHCID 178418287HCID 178418287, 화합물HCID 178461630HCID 178461630, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-255ec494d5f245e1888e65ce9141fd9c
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456169B2

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