Potassium Carbonate → Ethyl 4-[1-[4-[bis(4-isobutylphenyl)methoxy]benzoyl]indolizin-3-yl]butyrate

HRID 1741846Notes

Reaction equation

HRID 1741846 reaction equation
[OH:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([C:8]2[CH:9]=[C:10]([CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:11]3[C:16]=2[CH:15]=[CH:14][CH:13]=[CH:12]3)=[O:7])=[CH:4][CH:3]=1.[CH2:27]([C:31]1[CH:36]=[CH:35][C:34]([CH:37]([C:39]2[CH:44]=[CH:43][C:42]([CH2:45][CH:46]([CH3:48])[CH3:47])=[CH:41][CH:40]=2)Cl)=[CH:33][CH:32]=1)[CH:28]([CH3:30])[CH3:29].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:45]([C:42]1[CH:43]=[CH:44][C:39]([CH:37]([C:34]2[CH:35]=[CH:36][C:31]([CH2:27][CH:28]([CH3:30])[CH3:29])=[CH:32][CH:33]=2)[O:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([C:8]3[CH:9]=[C:10]([CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:11]4[C:16]=3[CH:15]=[CH:14][CH:13]=[CH:12]4)=[O:7])=[CH:25][CH:26]=2)=[CH:40][CH:41]=1)[CH:46]([CH3:48])[CH3:47]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11824313Ethyl 4-[1-(4-hydroxybenzoyl)indolizin-3-yl]butyrateHCID 19010817Bis(4-isobutylphenyl)chloromethane

Product 1

HCID 19010776Ethyl 4-[1-[4-[bis(4-isobutylphenyl)methoxy]benzoyl]indolizin-3-yl]butyrateYield 15.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 4-[1-(4-hydroxybenzoyl)indolizin-3-yl]butyrate (334 mg), bis(4-isobutylphenyl)chloromethane (599 mg) and potassium carbonate (394 mg) in N,N-dimethylformamide (5 ml) was stirred at room temperature for 20 hours. The reaction mixture was filtered and the filtrate was poured into a mixture of ethyl acetate and 0.5N hydrochloric acid. The organic layer was separated, washed with water and brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel eluting with n-hexane and ethyl acetate (3:1) to give ethyl 4-[1-[4-[bis(4-isobutylphenyl)methoxy]benzoyl]indolizin-3-yl]butyrate (95 mg) as an oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionthe filtrate was poured into a mixture of ethyl acetate and 0.5N hydrochloric acid
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue was chromatographed on silica gel eluting with n-hexane and ethyl acetate (3:1)

Sources & evidence

ORD record
ord-065ae1c4135b48129e74df8e2e205d67
Source dataset
uspto-grants-1994_08
Patent number
US05334716

Reaction notes

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