Methyl iodide → N-Methyl-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-2-pyrrolecarboxaldehyde

HRID 1857882Notes

Reaction equation

HRID 1857882 reaction equation
[CH3:1][C:2]1([CH3:21])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]3[CH:15]=[C:16]([CH:19]=[O:20])[NH:17][CH:18]=3)[CH:5]=[CH:4][C:3]1=2.[CH2:22]1COCC1.[H-].[Na+].IC>O>[CH3:22][N:17]1[CH:18]=[C:14]([C:6]2[CH:5]=[CH:4][C:3]3[C:2]([CH3:21])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]=3[CH:7]=2)[CH:15]=[C:16]1[CH:19]=[O:20]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 226346854-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-2-pyrrolecarboxaldehyde

Product 1

HCID 22634658N-Methyl-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-2-pyrrolecarboxaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.3 g (4.6 mmol) of 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-2-pyrrolecarboxaldehyde and 50 ml of THF are introduced into a three-necked flask under a stream of nitrogen. 300 mg (10 mmol) of sodium hydride (80% in oil) are added portionwise and the mixture is stirred until the evolution of gas has ceased. 640 μl (10 mmol) of iodomethane are then added and the mixture is stirred at room temperature for one hour. 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 dichloromethane and heptane (70/30). After evaporation of the solvents, 600 mg (44%) of the expected product are collected.

Workup

  1. stirringthe mixture is stirred at room temperature for one hour
  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 dichloromethane and heptane (70/30)
  9. customAfter evaporation of the solvents, 600 mg (44%) of the expected product
  10. customare collected

Sources & evidence

ORD record
ord-e324e1d52cc84e8ea8e520acd0b9387c
Source dataset
uspto-grants-2000_11
Patent number
US06147255

Reaction notes

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