Hydrochloric Acid → HCID 67598305, compound

HRID 362998Notes

Reaction equation

HRID 362998 reaction equation
[C:1]([O:4][CH:5]([C:13]1[O:17][C:16]2[CH:18]=[C:19]([O:22]CC3C=CC=CC=3)[CH:20]=[CH:21][C:15]=2[CH:14]=1)[CH2:6][O:7][CH2:8][CH2:9][N:10]([CH3:12])[CH3:11])(=[O:3])[CH3:2].Cl.CO.C(=O)([O-])O.[Na+]>[C].[Pd].O.C(Cl)(Cl)Cl>[C:1]([O:4][CH:5]([C:13]1[O:17][C:16]2[CH:18]=[C:19]([OH:22])[CH:20]=[CH:21][C:15]=2[CH:14]=1)[CH2:6][O:7][CH2:8][CH2:9][N:10]([CH3:12])[CH3:11])(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 516892Sodium BicarbonateHCID 54428525HCID 54428525, compound

Product 1

HCID 67598305HCID 67598305, compoundYield 63.4%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 3.2 g of 1-acetoxy-1-(6-benzyloxybenzo[b]furan-2-yl)-2-[2-(N,N-dimethylamino)ethoxy]ethane, 0.6 g of 5% palladium-carbon, 0.67 ml of concentrated hydrochloric acid and 30 ml of methanol was subjected to hydrogenation at room temperature under atmospheric pressure for 1.5 hours. After the completion of the reaction, the palladium-carbon was removed by filtration. The solvent was removed by distillation under reduced pressure. To the residue thus obtained were added 20 ml of chloroform and 20 ml of water. The resulting mixture was adjusted to pH 7 with sodium hydrogencarbonate. The organic layer was separated. The aqueous layer was extracted with 10 ml of chloroform. The extract was combined with the previously separated organic layer. The combined organic layer was washed with 5 ml of water, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by column chromatography (eluant: chloroform/methanol=7/1) to obtain 1.57 g of oily 1-acetoxy-1-(6-hydroxybenzo[b]furan-2-yl)-2-[2-(N,N-dimethylamino)ethoxy]ethane (compound No. 407).

Workup

  1. customAfter the completion of the reaction
  2. customthe palladium-carbon was removed by filtration
  3. customThe solvent was removed by distillation under reduced pressure
  4. customTo the residue thus obtained
  5. customThe organic layer was separated
  6. extractionThe aqueous layer was extracted with 10 ml of chloroform
  7. washThe combined organic layer was washed with 5 ml of water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was removed by distillation under reduced pressure
  10. customThe residue thus obtained
  11. customwas purified by column chromatography (eluant: chloroform/methanol=7/1)

Sources & evidence

ORD record
ord-704e89c6769341ef8be121d9b1fe618c
Source dataset
uspto-grants-1999_02
Patent number
US05872117

Reaction notes

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