Water → HCID 53745024, compound

HRID 342451Notes

Reaction equation

HRID 342451 reaction equation
[NH2:1][C:2]1[C:10]2[O:9][C:8]3[CH2:11][CH2:12][CH2:13][CH2:14][C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:15][C:16](=O)[CH2:17][CH2:18][C:19](=O)[CH3:20].O.C(=O)(O)[O-].[Na+]>Cl.C(O)C>[CH3:20][C:19]1[N:1]([C:2]2[C:10]3[O:9][C:8]4[CH2:11][CH2:12][CH2:13][CH2:14][C:7]=4[C:6]=3[CH:5]=[CH:4][CH:3]=2)[C:16]([CH3:15])=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 962WaterHCID 80352,5-HexanedioneHCID 516892Sodium BicarbonateHCID 31596706,7,8,9-TETRAHYDRODIBENZO[B,D]FURAN-4-AMINE

Product 1

HCID 53745024HCID 53745024, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

A mixture of 6-amino-1,2,3,4-tetrahydrodibenzofuran (230 mg), 2,5-hexanedione (145 mg) and conc. hydrochloric acid (1 drop) in ethanol (3 ml) was refluxed for 1 hour and poured into water. The mixture was neutralized with aqueous saturated sodium bicarbonate and extracted with ethyl acetate. The extract was washed with brine, dried over sodium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel and the obtained oil was crystallized from a mixture of ethanol and water to give 6-(2,5-dimethylpyrol-1-yl)-1,2,3,4-tetrahydrodibenzofuran (235 mg).

Workup

  1. temperaturewas refluxed for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel
  7. customthe obtained oil was crystallized from a mixture of ethanol and water

Sources & evidence

ORD record
ord-bd1297736a4f4023a7008a106149f155
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

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