Water → Diethyl 1-(2-methyl-6-quinolinyl)-1,2-cyclopropanedicarboxylate

HRID 1715196Notes

Reaction equation

[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[CH2:9]([O:11][C:12](=[O:31])[C:13]([C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[N:26]=[C:25]([CH3:30])[CH:24]=[CH:23]2)=[CH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:10].O>CS(C)=O>[CH3:30][C:25]1[CH:24]=[CH:23][C:22]2[C:27](=[CH:28][CH:29]=[C:20]([C:13]3([C:12]([O:11][CH2:9][CH3:10])=[O:31])[CH2:4][CH:14]3[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:21]=2)[N:26]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (0.52 g) was added in small portions to a stirred suspension of trimethylsulfoxonium iodide (2.81 g) in DMSO (28 mL) at room temperature. After 0.5 h, the clear reaction mixture was cooled to 0° C. and a solution of diethyl-2-(2-methyl-6-quinolinyl)-2-butenedioate (2.0 g) in DMSO (14 mL) was quickly added and the stirring continued for 0.5 h after which time water (30 mL) was added. The mixture was extracted twice with ether (30 mL), the organic phase was washed with saturated ammonium chloride, dried over sodium sulphate and evaporated under reduced pressure to give 2 g of the title product which was used without further purification.

Workup

waitthe stirring continued for 0.5 h
extractionThe mixture was extracted twice with ether (30 mL)
washthe organic phase was washed with saturated ammonium chloride
dry with materialdried over sodium sulphate
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-8b240249968f40da997390c92ef480c3
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07799815B2

Reaction notes

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