Water → N-Methoxy-N-methyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)cyclopropanecarboxamide

HRID 2268225Notes

Reaction equation

HRID 2268225 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[CH3:9][O:10][N:11]([CH3:30])[C:12](=[O:29])/[CH:13]=[CH:14]/[C:15]1[CH:24]=[CH:23][C:22]2[C:21]([CH3:26])([CH3:25])[CH2:20][CH2:19][C:18]([CH3:28])([CH3:27])[C:17]=2[CH:16]=1.O>CS(C)=O>[CH3:9][O:10][N:11]([CH3:30])[C:12]([CH:13]1[CH2:2][CH:14]1[C:15]1[CH:24]=[CH:23][C:22]2[C:21]([CH3:25])([CH3:26])[CH2:20][CH2:19][C:18]([CH3:28])([CH3:27])[C:17]=2[CH:16]=1)=[O:29]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 18349873(E)-N-Methoxy-N-methyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)acrylamide

Product 1

HCID 18349866N-Methoxy-N-methyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)cyclopropanecarboxamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

660 mg (3.3 mmol) of trimethylsulphoxonium iodide and 3 ml of DMSO are introduced into a three-necked flask under a stream of nitrogen. 100 mg (4.12 mmol) of sodium hydride (80% in oil) are added portionwise and the mixture is stirred until the evolution of gas has ceased. A solution of 900 mg (3 mmol) of (E)-N-methoxy-N-methyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)acrylamide in 15 ml of DMSO is then added dropwise and the mixture is stirred at room temperature for two hours. The reaction medium is poured into water and extracted with ethyl acetate, and the organic phase is separated out after settling has taken place, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (80/20). After evaporating the solvents, 400 mg (43%) of N-methoxy-N-methyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)cyclopropanecarboxamide are collected in the form of an oil.

Workup

  1. stirringthe mixture is stirred at room temperature for two hours
  2. extractionextracted with ethyl acetate
  3. customthe organic phase is separated out after settling
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a column of silica
  8. washeluted with a mixture of heptane and ethyl acetate (80/20)
  9. customAfter evaporating the solvents, 400 mg (43%) of N-methoxy-N-methyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)cyclopropanecarboxamide
  10. customare collected in the form of an oil

Sources & evidence

ORD record
ord-5f0297c26cfc4c648027821247d3f050
Source dataset
uspto-grants-2001_12
Patent number
US06326510B1

Reaction notes

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