Formaldehyde → Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine

HRID 1587367Notes

Reaction equation

HRID 1587367 reaction equation
[CH2:1]=O.[CH2:3]([NH:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CO.[C:18](=[O:21])([O-])[O-].[K+].[K+]>CCOCC>[CH2:3]([N:10]([CH2:1][O:21][CH3:18])[CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 887MethanolHCID 11430Potassium CarbonateHCID 353458N-[(Trimethylsilyl)methyl]benzylamine

Product 1

HCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A stirred 37% aqueous formaldehyde solution (230 g, 215 ml, 2.8 mole) was cooled to -5° C. and treated dropwise over 20 minutes with N-benzyl-N-[(trimethylsilyl)methyl]amine (D7, 380 g, 1.96 mole), whilst keeping the temperature between -5° and 0° C. After completing the addition, the mixture was treated with methanol (230 ml), saturated with potassium carbonate and stirred at room temperature for 2 h. The mixture was treated with ether (500 ml) and the organic phase separated, dried (K2CO3) and concentrated in vacuo to give a colourless oil (480 g), which was about 75% title compound (D8). This material was used in the next stage without purification.

Workup

  1. customthe temperature between -5° and 0° C
  2. additionthe addition
  3. customthe organic phase separated
  4. dry with materialdried (K2CO3)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-13e97adbfa0643ce857b12f758827bc2
Source dataset
uspto-grants-1993_06
Patent number
US05217975

Reaction notes

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