Sodium hydride → rac-ethyl (1R,2R)-2-(4-methoxyphenyl)cyclopropane-1-carboxylate

HRID 471425

Reaktionsgleichung

Reaktionsgleichung von HRID 471425
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[CH2:9]([O:11][C:12](=[O:23])[CH:13]=[CH:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[CH3:10]>CS(C)=O.O>[CH2:9]([O:11][C:12]([C@@H:13]1[CH2:2][C@H:14]1[C:15]1[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)=[O:23])[CH3:10]

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 74728Ethyl 4-methoxycinnamate

Produkt 1

HCID 818082rac-ethyl (1R,2R)-2-(4-methoxyphenyl)cyclopropane-1-carboxylateAusbeute 26,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

Trimethylsulfoxonium iodide (14.15 g, 63 mmol) is suspended in dry DMSO (126 mL) and Sodium hydride (60% in mineral oil, 2.52 g, 63 mmol) is added. The mixture is stirred for 40 minutes and then a solution of 4-methoxycinnamic acid ethyl ester (5 g, 24.2 mmol) in dry DMSO (64 mL) is added and the mixture stirred for 3 hours at room temperature. The mixture is diluted with water and extracted with ethyl acetate, the organic phase is dried by passing through a phase seperator and the solvent is removed under vacuum. The residue is purified by flash chromatography (10% ethyl acetate in cyclohexane) to give the title compound (yield 1.43 g).

Aufarbeitung

  1. stirringthe mixture stirred for 3 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. customthe organic phase is dried
  4. customthe solvent is removed under vacuum
  5. customThe residue is purified by flash chromatography (10% ethyl acetate in cyclohexane)

Quellen und Nachweise

ORD-Eintrag
ord-18e8175939e444b8b598cd845679290a
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633182B2

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