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

HRID 235515Notes

Reaction equation

HRID 235515 reaction equation
[OH:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[O:4][N:3]=1.[CH3:11][O:12][CH2:13]Cl>O1CCCC1.ClCCl>[CH3:11][O:12][CH2:13][O:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[O:4][N:3]=1

Participants

5

Reactant 2

HCID 7864Chloromethyl Methyl EtherHCID 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-diisopropylethylamino 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) δ3.57 (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-c7c1af49c5a447f183f419f5d9413511
Source dataset
uspto-grants-1997_01
Patent number
US05597926

Reaction notes

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