Acetic Acid → HCID 18786144, compound

HRID 1721591Notes

Reaction equation

HRID 1721591 reaction equation
[O:1]1[C:5]2[C:6]([CH2:10][C:11]([NH:13][CH3:14])=O)=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.[BH4-].[Na+].C(O)(=O)C.Cl>O1CCOCC1>[O:1]1[C:5]2[C:6]([CH2:10][CH2:11][NH:13][CH3:14])=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 22413362HCID 22413362, compound

Product 1

HCID 18786144HCID 18786144, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

8.70 g benzofuran-7-yl-N-methylacetamide and 5.21 g (0.138 mol) sodiumborohydride were dissolved in 100 ml dioxane. Acetic acid was added dropwise to the chilled solution. Then, the reaction mixture was warmed slowly and refluxed for 1 h. After cooling to room temperature, 25 ml 6N HCl was added and the mixture was warmed to reflux for 5 min. The mixture was cooled, pH adjusted to 10 and the mixture was extracted with dichloromethane. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated in vacuo. The remaining oil was distilled (B.p. 111-114° C/l mm Hg). The compound was obtained as colourless oil, 3.7 g (46%).

Workup

  1. temperatureThen, the reaction mixture was warmed slowly
  2. temperaturerefluxed for 1 h
  3. temperaturethe mixture was warmed
  4. temperatureto reflux for 5 min
  5. temperatureThe mixture was cooled
  6. extractionthe mixture was extracted with dichloromethane
  7. washThe organic layer was washed with water and brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. distillationThe remaining oil was distilled (B.p. 111-114° C/l mm Hg)
  11. customThe compound was obtained as colourless oil, 3.7 g (46%)

Sources & evidence

ORD record
ord-ea2038dbce184f3494f3c004efdbec43
Source dataset
uspto-grants-1996_04
Patent number
US05512562

Reaction notes

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