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

HRID 625705

Reaction equation

HRID 625705 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

HCID 818082rac-ethyl (1R,2R)-2-(4-methoxyphenyl)cyclopropane-1-carboxylateYield 26.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

Trimethylsulfoxonium iodide (14.15 g, 63 mmol) is suspended in dry dimethylsulfoxide (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 dimethylsulfoxide (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 separator 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). LC (METHOD 11): tR=7.74 min; Mass spectrum (ESI+): m/z=221 [M+H]+.

Workup

  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)

Sources & evidence

ORD record
ord-72d86a7f6e5945959a4859acfa28ee3d
Source dataset
uspto-grants-2016_04
Patent number
US09308194B2

Linked notes

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