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Ethanethiol → Ethyl 4-[1-(4-hydroxybenzoyl)indolizin-3-yl]butyrate

HRID 1741815
Notes
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Reaction equation

HRID 1741815 reaction equation
C[O:2][C:3]1[CH:27]=[CH:26][C:6]([C:7]([C:9]2[CH:10]=[C:11]([CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:12]3[C:17]=2[CH:16]=[CH:15][CH:14]=[CH:13]3)=[O:8])=[CH:5][CH:4]=1.C(S)C.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([C:9]2[CH:10]=[C:11]([CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:12]3[C:17]=2[CH:16]=[CH:15][CH:14]=[CH:13]3)=[O:8])=[CH:26][CH:27]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 19010853HCID 19010853, compound

Product 1

HCID 11824313Ethyl 4-[1-(4-hydroxybenzoyl)indolizin-3-yl]butyrateYield 55.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of ethyl 4-[1-(4-methoxybenzoyl)-indolizin-3-yl]butyrate (640 mg) and ethanethiol (2.5 ml) in dichloromethane (8 ml) was added aluminum chloride (700 mg) at 0° C. After stirred at 0° C. for 10 minutes, the solvent was evaporated and the residue was poured into a mixture of ethyl acetate and ice-water. The organic layer was separated, washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel column eluting with a mixture of chloroform and ethyl acetate (4:1) to give ethyl 4-[1-(4-hydroxybenzoyl)indolizin-3-yl]butyrate (344 mg) as yellow solid.

Workup

  1. customthe solvent was evaporated
  2. additionthe residue was poured into a mixture of ethyl acetate and ice-water
  3. customThe organic layer was separated
  4. washwashed with aqueous sodium bicarbonate and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue was chromatographed on silica gel column
  8. washeluting with a mixture of chloroform and ethyl acetate (4:1)

Sources & evidence

ORD record
ord-4eb4a9310a6f40f6ae9400f4148f966c
Source dataset
uspto-grants-1994_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05334716

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes