Formaldehyde → N-(methoxymethyl)-N-((trimethylsilyl)methyl)prop-2-en-1-amine

HRID 2425527Notes

Reaction equation

HRID 2425527 reaction equation
[CH3:1][Si:2]([CH2:5][NH:6][CH2:7][CH:8]=[CH2:9])([CH3:4])[CH3:3].[CH2:10]=O.CO.[C:14]([O-:17])([O-])=O.[K+].[K+]>COC(C)(C)C.O>[CH3:10][O:17][CH2:14][N:6]([CH2:5][Si:2]([CH3:4])([CH3:3])[CH3:1])[CH2:7][CH:8]=[CH2:9]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 887MethanolHCID 11430Potassium CarbonateHCID 12489587N-((trimethylsilyl)methyl)prop-2-en-1-amine

Product 1

HCID 18374742N-(methoxymethyl)-N-((trimethylsilyl)methyl)prop-2-en-1-amineYield 87.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To N-((trimethylsilyl)methyl)prop-2-en-1-amine (21 g, 146.5 mmol) was slowly added aqueous formaldehyde (20 g; 37% w/w) while stirring at room temperature. After 5 minutes additional stirring methanol (8 g) was added followed by the addition of K2CO3 (24 g). The reaction mixture was stirred overnight at room temperature. Water (100 ml) was added, followed by addition of tert-butyl methyl ether (75 ml). The organic layer was separated. The aqueous layer was extracted with tert-butyl methyl ether (75 ml). The combined organic extracts were dried with Na2SO4. Concentration under vacuum gave N-(methoxymethyl)-N-((trimethylsilyl)methyl)prop-2-en-1-amine as a clear oil (24 g, 128.1 mmol) in 87% c.y.

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred overnight at room temperature
  3. customThe organic layer was separated
  4. extractionThe aqueous layer was extracted with tert-butyl methyl ether (75 ml)
  5. dry with materialThe combined organic extracts were dried with Na2SO4
  6. concentrationConcentration under vacuum

Sources & evidence

ORD record
ord-2737a701769245c38e20c84ef9225fa2
Source dataset
uspto-grants-2011_06
Patent number
US07964739B2

Reaction notes

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