Diisopropylethylamine → HCID 19010823, compound

HRID 1741848Notes

Reaction equation

HRID 1741848 reaction equation
[OH:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([C:8]2[N:16]3[C:11]([CH:12]=[CH:13][CH:14]=[CH:15]3)=[C:10]([CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:9]=2)=[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(N(C(C)C)CC)(C)C>ClCCl>[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[N:16]4[C:11]([CH:12]=[CH:13][CH:14]=[CH:15]4)=[C:10]([CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:9]=3)=[O:7])=[CH:25][CH:26]=2)=[CH:40][CH:41]=1)[CH:46]([CH3:48])[CH3:47]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 19010817Bis(4-isobutylphenyl)chloromethaneHCID 19010833HCID 19010833, compound

Product 1

HCID 19010823HCID 19010823, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl 4-[3-(4-hydroxybenzoyl]indolizin-1-yl]butyrate (400 mg), bis(4-isobutylphenyl)chloromethane (430 mg) and diisopropylethylamine (736 mg) in dichloromethane (20 ml) was refluxed for 14 hours and evaporated. The residue was dissolved in ethyl acetate. The solution was 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 (4:1) to give ethyl 4-[3-[4-[bis(4-isobutylphenyl)methoxy]benzoyl]indolizin-1-yl]butyrate (158 mg) as an oil.

Workup

  1. temperaturewas refluxed for 14 hours
  2. customevaporated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washThe solution was washed 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 (4:1)

Sources & evidence

ORD record
ord-94938173f370442c9ba896e3ecba1898
Source dataset
uspto-grants-1994_08
Patent number
US05334716

Reaction notes

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