1-(Chloromethoxy)-2-methoxyethane → HCID 90402630, compound

HRID 1049265Notes

Reaction equation

HRID 1049265 reaction equation
[CH:1]([C:4]1[NH:5][CH:6]=[CH:7][N:8]=1)([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[CH3:18][O:19][CH2:20][CH2:21][O:22][CH2:23]Cl>C(Cl)Cl>[CH:1]([C:4]1[N:5]([CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])[CH:6]=[CH:7][N:8]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 81531DiisopropylethylamineHCID 1234571H-Imidazole, 2-(1-methylethyl)-

Product 1

HCID 90402630HCID 90402630, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-isopropylimidazole (3.0 g, 27.2 mmol) and DIEA (5.28 g, 40.9 mmol) in DCM (75 mL) was treated drop-wise with methoxyethoxymethyl chloride [MEM-Cl] (4.24 g, 34.0 mmol) and stirred at RT for 16 h. The mixture was washed with water, then brine, dried over Na2SO4 and concentrated to dryness to afford 2-isopropyl-1-((2-methoxyethoxy)methyl)-1H-imidazole (3.91 g, 72%). 1H NMR (400 MHz, DMSO-d6): δ 7.11 (d, J=1.3 Hz, 1H), 6.74 (d, J=1.3 Hz, 1H), 5.30 (s, 2H), 3.47-3.46 (m, 2H), 3.38-3.37 (m, 2H), 3.19 (s, 3H), 3.08-3.07 (m, 1H), 1.18 (d, J=6.8 Hz, 6H).

Workup

  1. washThe mixture was washed with water
  2. dry with materialbrine, dried over Na2SO4
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-7ae8365c9869485e88361634dace94f6
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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