Water → 7-Chloro-2-[(E)-2-(3-oxiranyl-phenyl)-vinyl]-quinoline

HRID 512918Notes

Reaction equation

HRID 512918 reaction equation
[I-].[CH3:2][S+](C)C.[H-].[Na+].[Cl:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15](/[CH:19]=[CH:20]/[C:21]3[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=3)[CH:24]=[O:25])=[N:16]2)=[CH:11][CH:10]=1.O>CS(C)=O.C1COCC1.C(OCC)(=O)C>[Cl:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15](/[CH:19]=[CH:20]/[C:21]3[CH:28]=[CH:27][CH:26]=[C:23]([CH:24]4[CH2:2][O:25]4)[CH:22]=3)=[N:16]2)=[CH:11][CH:10]=1

Participants

8

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodideHCID 100173053-[(E)-2-(7-Chloroquinolin-2-yl)ethenyl]benzaldehyde

Product 1

HCID 867207317-Chloro-2-[(E)-2-(3-oxiranyl-phenyl)-vinyl]-quinolineYield 66.7%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of trimethylsulphonium iodide (7.66 g, 37.54 mmol) in dry DMSO (50 ml), under nitrogen was added 50% sodium hydride (1.8 g, 37.54 mmol). The solution was cooled to 10° C. A suspension of 3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-benzaldehyde 29 (10.0 g, 34.12 mmol) in THF (50 ml) was added to the above solution in one portion. The reaction mixture was stirred at ambient conditions for 2 hours and poured into water (1.0 L) followed by usual work in ethyl acetate, and FC to give the epoxide 30 (7.0 g, 66%) as a cream colored solid.

Workup

  1. additionwas added to the above solution in one portion

Sources & evidence

ORD record
ord-de11262d8fd944fe8292d14eb81d6597
Source dataset
uspto-grants-2015_08
Patent number
US09102665B2

Reaction notes

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