2,5-Dimethoxytetrahydrofuran → HCID 19744592, compound

HRID 2254461Notes

Reaction equation

HRID 2254461 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]([CH3:12])=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].CO[CH:15]1[CH2:19][CH2:18][CH:17](OC)O1.CCCCCC.C(OCC)(=O)C>C(O)(=O)C>[N:1]1([C:2]2[CH:3]=[C:4]([C:9]([CH3:12])=[CH:10][CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])[CH:15]=[CH:19][CH:18]=[CH:17]1

Participants

5

Reactant 3

HCID 790982,5-DimethoxytetrahydrofuranHCID 15049977Methyl 5-Amino-2-methylbenzoateHCID 21226206Ethyl acetate hexane

Product 1

HCID 19744592HCID 19744592, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

158 mg of methyl 3-amino-6-methylbenzoate was dissolved in 3 ml of acetic acid, and 139 mg of 2,5-dimethoxytetrahydrofuran was added. The mixture was heated under reflux for 1 hour. The reaction mixture was evaporated to dryness under reduced pressure. The residue was purified by silica gel column chromatography Wakogel C-200, 10 g; eluting solvent: hexane/ethyl acetate=10/1) to give 185 mg (yield 87%) of methyl 3-(1-pyrrolyl)-6-methylbenzoate, m.p. 56°-57° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. customThe reaction mixture was evaporated to dryness under reduced pressure
  4. customThe residue was purified by silica gel column chromatography Wakogel C-200, 10 g

Sources & evidence

ORD record
ord-e0c4d73ab87e4a359f00d59ffce35bae
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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