Chloromethyl Methyl Ether → Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine

HRID 1066909Notes

Reaction equation

HRID 1066909 reaction equation
C([Li])CCC.[CH2:6]([NH:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:19][O:20][CH2:21]Cl>C1COCC1>[CH2:6]([N:13]([CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH2:19][O:20][CH3:21])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 353458N-[(Trimethylsilyl)methyl]benzylamineHCID 178418339Butyllithium

Product 1

HCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineYield 75.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

n-Butyllithium (1.6 M solution in hexane, 34.85 mL, 55.76 mmol) was added to N-benzyltrimethylsilylmethylamine (10 g, 55.76 mmol) in dry THF (140 mL) and stirred at −78° C. under nitrogen atmosphere. After 45 minutes, methoxymethyl chloride (4.3 mL, 55.76 mmol) in THF (6 mL) was added and then stirred for another 3 hours. The THF was evaporated, and the residue was dissolved in hexane, washed with water, and dried over sodium sulfate. The solvent was evaporated to give under reduced pressure to give N-benzyl-N-(methoxymethyl)trimethylsilylmethylamine (10 g).

Workup

  1. stirringstirred for another 3 hours
  2. customThe THF was evaporated
  3. dissolutionthe residue was dissolved in hexane
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated
  7. customto give under reduced pressure

Sources & evidence

ORD record
ord-e0d7da2ebd8048318e98c16e5dad161c
Source dataset
uspto-grants-2001_06
Patent number
US06245801B1

Reaction notes

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