Chloromethyl Methyl Ether → Methyl 3-(Methoxymethoxy)-5-isoxazole Carboxylate

HRID 52840Notes

Reaction equation

HRID 52840 reaction equation
[OH:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[O:4][N:3]=1.C(N(CC)C(C)C)(C)C.[CH3:20][O:21][CH2:22]Cl>O1CCCC1.ClCCl>[CH3:20][O:21][CH2:22][O:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[O:4][N:3]=1

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 178498603HCID 178498603, compound

Product 1

HCID 18939647Methyl 3-(Methoxymethoxy)-5-isoxazole CarboxylateYield 78%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.0 g (14.0 mmol) of methyl 3-hydroxy-5-isoxazole carboxylate and 29.2 ml (16.8 mmol) of N,N-diisopropylethylamine in 20 ml of tetrahydrofuran was treated with 1.27 ml of chloromethyl methyl ether. After being stirred at ambient temperature for 2 h, the solution was diluted with dichloromethane, washed with water, dried over MgSO4, and concentrated in vacuo. Silica gel chromatography of the residue using 10% methanol in dichloromethane provided 129.6 mg (78%) of the desired compound as a white solid. 1H NMR (CDCl3) δ 3.57 (s, 3H), 3.96 (s, 3H), 5.37 (s, 2H), 6.64 (s, 1H).

Workup

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-57d4d0d7196d43deaaa29145a5863f70
Source dataset
uspto-grants-1997_04
Patent number
US05616714

Reaction notes

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