Diisopropylethylamine → 1-(1-{[2-(Trimethylsilyl)ethoxy]methyl}imidazol-2-yl)ethanone

HRID 1398562Notes

Reaction equation

HRID 1398562 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6](=[O:8])[CH3:7].CCN(C(C)C)C(C)C.[CH3:18][Si:19]([CH2:22][CH2:23][O:24][CH2:25]Cl)([CH3:21])[CH3:20].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:18][Si:19]([CH3:21])([CH3:20])[CH2:22][CH2:23][O:24][CH2:25][N:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6](=[O:8])[CH3:7]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 5389722-AcetylimidazoleHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 598646231-(1-{[2-(Trimethylsilyl)ethoxy]methyl}imidazol-2-yl)ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(1H-imidazol-2-yl)ethanone (550 mg, 4.99 mmol), 3.18 mmol) in DCM (20 mL) was added DIPEA (1.74 ml, 9.99 mmol) and SEM chloride (0.87 ml dissolved in 5 mL DCM, 4.99 mmol). The resulting mixture was stirred at RT for 1 hr. Saturated aqueous sodium bicarbonate (10 mL) was then added and the aqueous phase was extracted with DCM (3×10 mL extractions). The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo to give the title intermediate as a yellow oil: 1H NMR (500 MHz, CDCl3) delta 0.00 (9H, s), 1.03-0.82 (2H, m), 2.66 (3H, s), 3.66-3.38 (2H, m), 5.76 (2H, s), 7.18 (1H, s), 7.28 (1H, s); LC-MS: m/z=+241.00 (M+H)+.

Workup

  1. extractionthe aqueous phase was extracted with DCM (3×10 mL extractions)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0945dcae66a446478f03a7d5cb0d7e6f
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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