Pyridine → trans 1-[2-(5-Chloro-thiophen-2-yl)-cyclopropyl]-ethanone O-methyl-oxime

HRID 1807403Notes

Reaction equation

HRID 1807403 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C@@H:7]2[CH2:9][C@H:8]2[C:10](=O)[CH3:11])=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl.[CH3:20][O:21][NH2:22]>CO>[CH3:20][O:21][N:22]=[C:10]([C@@H:8]1[CH2:9][C@H:7]1[C:5]1[S:6][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH3:11]

Participants

5

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 51723384trans 1-[2-(5-Chloro-thiophen-2-yl)-cyclopropyl]-ethanone

Product 1

HCID 86669077trans 1-[2-(5-Chloro-thiophen-2-yl)-cyclopropyl]-ethanone O-methyl-oximeYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of trans 1-[2-(5-chloro-thiophen-2-yl)-cyclopropyl]-ethanone (1.0 g; 5.0 mmol) in methanol (10 ml) at ambient temperature was added pyridine (0.85 ml; 10.3 mmol) and methoxyamine hydrochloride (0.86 g; 10.3 mmol). The reaction mixture was stirred for 20 hours at ambient temperature then poured on water (50 ml) and extracted with dichloromethane (3×20 ml). Combined organic layers were dried over anhydrous sodium sulphate. The solvent was removed in vacuo to afford 1.0 g (92% of theory) of trans 1-[2-(5-Chloro-thiophen-2-yl)-cyclopropyl]-ethanone O-methyl-oxime as an E/Z mixture in form of a clear oil.

Workup

  1. additionthen poured on water (50 ml)
  2. extractionextracted with dichloromethane (3×20 ml)
  3. dry with materialCombined organic layers were dried over anhydrous sodium sulphate
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-fdb2a3c6c11d4e0488e7c94f2e7786a4
Source dataset
uspto-grants-2013_01
Patent number
US08357635B2

Reaction notes

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