Methyl iodide → [4-(Cyclopropylcarbonyl)pheny]methyl-propanedioic acid, dimethyl ester

HRID 1581851Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1581851
[CH:1]1([C:4]([C:6]2[CH:11]=[CH:10][C:9]([CH2:12][C:13](OC)=O)=[CH:8][CH:7]=2)=[O:5])[CH2:3][CH2:2]1.CO[C:19](=[O:22])[O:20][CH3:21].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].IC>O1CCCC1.C(OCC)(=O)C.O>[CH:1]1([C:4]([C:6]2[CH:7]=[CH:8][C:9]([CH2:12][CH:13]([C:19]([O:20][CH3:21])=[O:22])[C:19]([O:20][CH3:21])=[O:22])=[CH:10][CH:11]=2)=[O:5])[CH2:2][CH2:3]1

Komponenten

8

Edukt 4

HCID 6328Methyl iodideHCID 12021Dimethyl CarbonateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 12096482Methyl 2-(4-(cyclopropanecarbonyl)phenyl)acetate

Produkt 1

HCID 67524057[4-(Cyclopropylcarbonyl)pheny]methyl-propanedioic acid, dimethyl esterAusbeute 21,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Dissolve 4-(cyclopropylcarbonyl)benzeneacetic acid, methyl ester (1.5 g, 6.0 mmol) and dimethylcarbonate (930 mg, 10.3 mmol) in tetrahydrofuran (10 mL). Add 20 mL (20 mmol) of a 1.0 molar solution of sodium bis(trimethylsilyl)amide in tetrahydrofuran over 0.5 hours. Stir 3 days. Add iodomethane (5.3 g, 35 mmol). Stir 24 hours. Add water and ethyl acetate. Wash organic phase with brine, dry over anhydrous magnesium sulfate and concentrate. Purify by flash chromatography (50 g silica gel, ethyl acetate/heptane as eluent) to give the title compound (315 mg, 16%).

Aufarbeitung

  1. stirringStir 24 hours
  2. dry with materialWash organic phase with brine, dry over anhydrous magnesium sulfate
  3. concentrationconcentrate
  4. customPurify by flash chromatography (50 g silica gel, ethyl acetate/heptane as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-9d9409a266364dde867ffbe9fd00471c
Quelldatensatz
uspto-grants-2004_05
Patentnummer
US06730791B2

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