Sodium hydride → trans-Methyl 2-(quinolin-2-yl)cyclopropanecarboxylate

HRID 718704Notes

Reaction equation

HRID 718704 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1/[CH:19]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22]>CS(C)=O.CCOC(C)=O>[N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1[C@@H:19]1[CH2:2][C@H:20]1[C:21]([O:23][CH3:24])=[O:22]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 6479253Methyl (E)-3-(2-quinolinyl)-2-propenoate

Product 1

HCID 117728668trans-Methyl 2-(quinolin-2-yl)cyclopropanecarboxylate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tri-methylsulfoxonium iodide (495 mg, 2.25 mmol) in DMSO (4 mL) was added NaH (90 mg, 2.2 mmol) and the resulting mixture was stirred for 30 min. At this time compound 79a (400 mg, 1.87 mmol) was added in one portion and the resulting mixture was stirred overnight. The reaction mixture was then diluted with EtOAc (100 mL), washed with saturated sodium bicarbonate (100 mL) and concentrated in vacuo to obtain a residue which was purified by flash column chromatography on silica gel (0-50% EtOAc-heptane) to afford compound 79b as a white solid. Mass spectrum (LCMS, ESI pos.) Calcd. For C14H13NO2 228.0 (M+H). found 228.2.

Workup

  1. stirringthe resulting mixture was stirred overnight
  2. washwashed with saturated sodium bicarbonate (100 mL)
  3. concentrationconcentrated in vacuo
  4. customto obtain a residue which
  5. customwas purified by flash column chromatography on silica gel (0-50% EtOAc-heptane)

Sources & evidence

ORD record
ord-2faa6eade79c40739915d7bf77bd0109
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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