Acetyl chloride → Diisopropylether methanol

HRID 276911

Reaction equation

HRID 276911 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[NH:9]1[C:17]2[CH:16]=[CH:15][CH:14]=[C:13]3[CH2:18][CH2:19][CH2:20][CH:11]([C:12]=23)[C:10]1=[O:21].[CH:22]([O:25][CH:26]([CH3:28])[CH3:27])([CH3:24])[CH3:23]>C(OCC)(=O)C.C(=S)=S>[CH3:1][OH:3].[CH:22]([O:25][CH:26]([CH3:28])[CH3:27])([CH3:24])[CH3:23].[C:1]([C:14]1[CH:15]=[CH:16][C:17]2[NH:9][C:10](=[O:21])[CH:11]3[CH2:20][CH2:19][CH2:18][C:13]=1[C:12]=23)(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 6367Acetyl chlorideHCID 7914Diisopropyl EtherHCID 5993752a,3,4,5-Tetrahydrobenzo[cd]indol-2(1H)-oneHCID 6451240Aluminum(III) Chloride

Product 2

HCID 21882575Diisopropylether methanolHCID 226295716-Acetyl-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one

Reagents, catalysts & solvents 2

HCID 6348Carbon DisulfideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A 3.1 ml (43.4 mmol) portion of acetyl chloride was added to a carbon disulfide suspension (100 ml) of aluminum chloride (11.5 g, 86.7 mmol) and stirred at a room temperature for 30 minutes. Thereto was added dropwise a carbon disulfide solution (150 ml) of 2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one (5.0 g, 28.9 mmol) spending 2 hours. After 2 hours of heating under reflux and confirmation of the disappearance of the material by a thin layer chromatography, this was returned to a room temperature and mixed with isopropyl ether. The supernatant fluid was discarded by decantation, and the remaining rubber-like substance was dissolved in ethyl acetate and washed with water. The water layer was extracted with ethyl acetate, the organic layers were combined and dried (Na2SO4), and then the solvent was evaporated under a reduced pressure. By recrystallizing the thus obtained oily substance from ethyl acetate-isopropyl ether and then from methanol-isopropyl ether, 3.5 g of the title compound was obtained (yield, 56%).

Workup

  1. waitspending 2 hours
  2. temperatureAfter 2 hours of heating
  3. temperatureunder reflux
  4. customthis was returned to a room temperature
  5. washwashed with water
  6. extractionThe water layer was extracted with ethyl acetate
  7. dry with materialdried (Na2SO4)
  8. customthe solvent was evaporated under a reduced pressure
  9. customBy recrystallizing the thus obtained oily substance from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-22f89a4c340e44188cc12853f30910b2
Source dataset
uspto-grants-2002_03
Patent number
US06355642B1

Linked notes

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