Hydrochloric Acid → ethyl(E)-3-[1-(4-benzyloxybenzyl)-4-phenyl-3-pyrrolyl]propenoate

HRID 350030Notes

Reaction equation

HRID 350030 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:30]=[CH:29][C:14]([CH2:15][N:16]2[CH:20]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:18]([CH:27]=O)=[CH:17]2)=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(OP([CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])(OCC)=O)C.Cl>CN(C)C=O>[CH2:3]([O:10][C:11]1[CH:30]=[CH:29][C:14]([CH2:15][N:16]2[CH:20]=[C:19]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:18](/[CH:27]=[CH:39]/[C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:17]2)=[CH:13][CH:12]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 230249941-(4-Benzyloxybenzyl)-4-phenylpyrrole-3-carbaldehyde

Product 1

HCID 69421069ethyl(E)-3-[1-(4-benzyloxybenzyl)-4-phenyl-3-pyrrolyl]propenoateYield 94.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60%, oily, 2.13 g) was added to a mixture of 1-(4-benzyloxybenzyl)-4-phenylpyrrole-3-carbaldehyde (18.00 g), ethyl diethylphosphonoacetate (12.09 g) and N,N-dimethylformamide (150 ml) at 0° C., and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into dilute hydrochloric acid, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and then concentrated. The residue was subjected to silica gel column chromatography, and ethyl(E)-3-[1-(4-benzyloxybenzyl)-4-phenyl-3-pyrrolyl]propenoate (20.16 g, yield: 94%) was obtained as colorless crystals from the fraction eluted with ethyl acetate-hexane (1:4, volume ratio). This was recrystallized from ethyl acetate-hexane. Melting point: 111–112° C.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e921731164064093bfffcbe542b428f8
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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