2,5-Dimethoxytetrahydrofuran → HCID 20458193, compound

HRID 544726Notes

Reaction equation

HRID 544726 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:9][CH3:10])[CH:5]=[CH:6][C:7]=1[CH3:8].CO[CH:13]1[CH2:17][CH2:16][CH:15](OC)O1>C(O)(=O)C>[CH3:8][C:7]1[CH:6]=[CH:5][C:4]([O:9][CH3:10])=[CH:3][C:2]=1[N:1]1[CH:13]=[CH:17][CH:16]=[CH:15]1

Participants

4

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 995005-Methoxy-o-toluidine

Product 1

HCID 20458193HCID 20458193, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 88.4 g (0.64 mole) of 3-amino-4-methylanisole in 1.4 liters of glacial acetic acid is heated to 106° and, at this temperature, 114 g (0.86 mole) of 2,5-dimethoxytetrahydrofuran are added in the course of 30 minutes. The mixture is then immediately cooled to room temperature and concentrated in a vacuum rotary evaporator. Distillation of the residue in a high vacuum yields 4-methyl-3-(pyrrol-1-yl)-anisole, b.p. 93°-95°/0.04 torr. Rf (toluene/ethyl acetate=10:1): 0.57.

Workup

  1. additionare added in the course of 30 minutes
  2. concentrationconcentrated in a vacuum rotary evaporator
  3. distillationDistillation of the residue in a high vacuum

Sources & evidence

ORD record
ord-498399f7111c4cc99af8808e4111fb43
Source dataset
uspto-grants-1984_05
Patent number
US04451462

Reaction notes

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