Hydrochloric Acid → HCID 20255660, compound

HRID 637698Notes

Reaction equation

HRID 637698 reaction equation
Cl.[NH2:2][C:3]1[C:11]([CH3:12])=[CH:10][C:6]2[CH:7]=[CH:8][O:9][C:5]=2[CH:4]=1.CO[CH:15]1[CH2:19][CH2:18][CH:17](OC)O1>O1CCOCC1>[CH3:12][C:11]1[C:3]([N:2]2[CH:15]=[CH:19][CH:18]=[CH:17]2)=[CH:4][C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 790982,5-DimethoxytetrahydrofuranHCID 20255640HCID 20255640, compound

Product 1

HCID 20255660HCID 20255660, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2 ml of 6N hydrochloric acid are added to a mixture of 2.95 g (20 mmole) of 6-amino-5-methylbenzofuran, 3.17 g (24 mmole) of 2,5-dimethoxytetrahydrofuran and 50 ml of dioxane and the whole is boiled under reflux for 40 minutes. The whole is then concentrated in vacuo, the residue is taken up in methylene chloride and the organic phase is washed three times with water. The crude product remaining after drying and removal of the methylene chloride is chromatographed over silica gel with ether/petroleum ether. Subsequent distillation of the pure fractions in a bulb tube (105°, 5.10-2 torr) yields 5-methyl-6-(pyrrol-1-yl)-benzofuran in the form of a pale yellow oil.

Workup

  1. temperatureunder reflux for 40 minutes
  2. concentrationThe whole is then concentrated in vacuo
  3. washthe organic phase is washed three times with water
  4. customafter drying
  5. customremoval of the methylene chloride
  6. customis chromatographed over silica gel with ether/petroleum ether
  7. distillationSubsequent distillation of the pure fractions in a bulb tube (105°, 5.10-2 torr)

Sources & evidence

ORD record
ord-f85ea0571a424b46bf53f9740acdff7a
Source dataset
uspto-grants-1985_12
Patent number
US04558043

Reaction notes

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