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1,1'-Carbonyldiimidazole → Methyl 4-(4-chlorophenyl)-4-methyl-3-oxopentanoate

HRID 878732
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HRID 878732 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH3:12])[C:9]([OH:11])=O)=[CH:4][CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[Mg+2].[Cl-].[Cl-].[K+].[CH3:30][O:31][C:32](=[O:37])[CH2:33]C([O-])=O>C1COCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:13])([CH3:12])[C:9](=[O:11])[CH2:33][C:32]([O:31][CH3:30])=[O:37])=[CH:6][CH:7]=1
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참가 물질

7

반응물 4

HCID 682631,1'-CarbonyldiimidazoleHCID 804062-(4-Chlorophenyl)-2-methylpropionic acidHCID 2724687Potassium methyl malonateHCID 5360315Magnesium Chloride

생성물 1

HCID 86725679Methyl 4-(4-chlorophenyl)-4-methyl-3-oxopentanoate수율 23.3%

시약·촉매·용매 2

HCID 8028
Tetrahydrofuran
용매
HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 2-(4-chlorophenyl)-2-methylpropanoic acid (200 mg, 1.01 mmol) in THF (20 mL) was added CDI (172 mg, 1.06 mmol) at rt. The reaction mixture was stirred at rt for 2 h. Added MgCl2 (105 mg, 1.11 mmol) and 3-methoxy-3-oxopropanoic acid potassium salt (173 mg, 1.11 mmol) at rt. The mixture was stirred at 60° C. overnight. Dilute with ethyl acetate (100 mL), washed with 0.5 N HCl (20 mL×2) and brine (50 mL), dried over Na2SO4, filtered, concentrated, purified by flash column chromatography to give the title compound (60 mg, 23%) as a yellow oil. 1H NMR (300 MHz, CDCl3): δ 1.51 (6H, s), 3.28 (2H, s), 3.67 (3H, s), 7.20-7.30 (2H, m), 7.34-7.37 (2H, m).

후처리

  1. customat rt
  2. stirringThe mixture was stirred at 60° C. overnight
  3. washwashed with 0.5 N HCl (20 mL×2) and brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash column chromatography

출처 및 근거

ORD 기록
ord-ac72259de80a4b7a98d6aaeee31369db
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08987461B2

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