Acetyl chloride → HCID 19045291, compound

HRID 1781416Notes

Reaction equation

HRID 1781416 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[C:13](Cl)(=[O:15])[CH3:14].[Cl-].[Al+3].[Cl-].[Cl-].[BH4-].[Na+]>ClCCCl.O>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH:13]([CH3:14])[OH:15])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 276731-(2,3-Dihydro-1H-indol-1-yl)ethan-1-oneHCID 4311764Sodium borohydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 19045291HCID 19045291, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 962WaterSolvent

Procedure

1-Acetyl-2,3-dihydro-1H-indole (16.1 g, 0.1 mol) in 1,2-dichloroethane (60 ml) was added dropwise to refluxing mixture of acetyl chloride (21.33 ml, 23.55 g, 0.3 mol) and aluminum chloride (40.0 g, 0.3 mol) in 1,2-dichloroethane (40 ml). The mixture was heated under reflux for 2 hours, cooled and poured onto crushed ice (1 Kg). The mixture was extracted with dichloromethane (3×500 ml) and the combined organic fractions were dried (Na2SO4) and evaporated under reduced pressure. Ethanol (400 ml) was added and the mixture was cooled in a water bath. Sodium borohydride (7.57 g, 0.2 mol) was added and the mixture was stirred for 1 hour. Water (100 ml) was added and the ethanol was evaporated under reduced pressure. Water (500 ml) was added and the mixture was extracted with dichloromethane (3×500 ml) and the combined organic fractions were dried (Na2SO4) and evaporated under reduced pressure. The residue was recrystallized from ethyl acetate to give the alcohol as an off-white solid (18.43 g, 90%).

Workup

  1. temperatureto refluxing
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 2 hours
  4. temperaturecooled
  5. additionpoured
  6. extractionThe mixture was extracted with dichloromethane (3×500 ml)
  7. dry with materialthe combined organic fractions were dried (Na2SO4)
  8. customevaporated under reduced pressure
  9. additionEthanol (400 ml) was added
  10. temperaturethe mixture was cooled in a water bath
  11. customthe ethanol was evaporated under reduced pressure
  12. additionWater (500 ml) was added
  13. extractionthe mixture was extracted with dichloromethane (3×500 ml)
  14. dry with materialthe combined organic fractions were dried (Na2SO4)
  15. customevaporated under reduced pressure
  16. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-baf929c61250483a893cc2ec64cc1564
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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