Methyl iodide → t-Butyl [4-(2-ethoxyethoxy) phenethyl]-methylcarbamate

HRID 1197935Notes

Reaction equation

HRID 1197935 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:22]=[CH:21][C:10]([CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:9][CH:8]=1)[CH3:2].[CH3:23]I>CN(C)C=O>[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:22]=[CH:21][C:10]([CH2:11][CH2:12][N:13]([CH3:23])[C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[CH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 54133570t-Butyl [4-(2-ethoxyethoxy)phenethyl]carbamate

Product 1

HCID 53822661t-Butyl [4-(2-ethoxyethoxy) phenethyl]-methylcarbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.2 g of a 55% sodium hydride dispersion in oil were washed with hexane and covered with 190 ml of dimethylformamide. Thereafter, 19.0 g (61.6 mmol) of t-butyl [4-(2-ethoxyethoxy)phenethyl]carbamate in solid form were added while cooling with ice and stirring, the reaction mixture was stirred at room temperature for 15 minutes and subsequently treated dropwise with 5.7 ml of methyl iodide in 10 ml of dimethylformamide within 5 minutes. After completion of the addition the reaction mixture was stirred at room temperature for 18 hours and subsequently poured into ice-water and extracted with methylene chloride. The methylene chloride extracts were dried over magnesium sulfate and evaporated under reduced pressure, and the residue was chromatographed on 240 g of silica gel with a mixture of hexane and ethyl acetate as the eluting agent, whereby 19.5 g of t-butyl [4-(2-ethoxyethoxy) phenethyl]-methylcarbamate were obtained as an oil which was used directly in the next step.

Workup

  1. wash3.2 g of a 55% sodium hydride dispersion in oil were washed with hexane
  2. temperaturewhile cooling with ice
  3. stirringthe reaction mixture was stirred at room temperature for 15 minutes
  4. additionAfter completion of the addition the reaction mixture
  5. stirringwas stirred at room temperature for 18 hours
  6. extractionextracted with methylene chloride
  7. dry with materialThe methylene chloride extracts were dried over magnesium sulfate
  8. customevaporated under reduced pressure
  9. customthe residue was chromatographed on 240 g of silica gel with a mixture of hexane and ethyl acetate as the eluting agent

Sources & evidence

ORD record
ord-2810a6440b5e4314bc032076610300cd
Source dataset
uspto-grants-1994_01
Patent number
US05278148

Reaction notes

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