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p-Acetoxybenzoyl chloride → HCID 10862141, compound

HRID 1741824
Notes
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Reaction equation

HRID 1741824 reaction equation
[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9](Cl)=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[CH:18]1[CH:19]=[C:20]([CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[N:21]2[C:26]=1[CH:25]=[CH:24][CH:23]=[CH:22]2>ClCCl>[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([C:18]2[CH:19]=[C:20]([CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[N:21]3[C:26]=2[CH:25]=[CH:24][CH:23]=[CH:22]3)=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 2756254p-Acetoxybenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 11096444HCID 11096444, compound

Product 1

HCID 10862141HCID 10862141, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Acetoxybenzoyl chloride (53.6 g) was added to a suspension of aluminum chloride (36.5 g) in dichloromethane (500 ml). After the mixture was stirred for 20 minutes at room temperature, a solution of ethyl 4-(indolizin-3-yl)butyrate (57.8 g) in dichloromethane (50 ml) was added to the mixture. The mixture was stirred for 2 hours at room temperature and the solvent was evaporated. The residue was dissolved in ethyl acetate (500 ml) and washed with water. N,N-dimethylaminopropylamine (20 ml) was added to the solution. The mixture was washed with diluted hydrochloric acid, water, sodium bicarbonate aqueous solution and water. The solution was dried over magnesium sulfate and the solvent was removed in vacuo. The residue was washed with diisopropyl ether to give ethyl 4-[1-(4-acetoxybenzoyl)indolizin-3-yl]butyrate as yellow powder (36.5 g).

Workup

  1. stirringThe mixture was stirred for 2 hours at room temperature
  2. customthe solvent was evaporated
  3. dissolutionThe residue was dissolved in ethyl acetate (500 ml)
  4. washwashed with water
  5. additionN,N-dimethylaminopropylamine (20 ml) was added to the solution
  6. washThe mixture was washed with diluted hydrochloric acid, water, sodium bicarbonate aqueous solution and water
  7. dry with materialThe solution was dried over magnesium sulfate
  8. customthe solvent was removed in vacuo
  9. washThe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-bfa7df34696440778d928ef93ef90127
Source dataset
uspto-grants-1994_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05334716

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes