HCID 54057319, compound → HCID 53747219, compound

HRID 868286Notes

Reaction equation

HRID 868286 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:26])[CH:8]=[C:9]([CH:11]=[CH:12][CH2:13][C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[O:22]CCO)[CH:10]=1)=[O:5])[CH3:2]>FC(F)(F)C(O)=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:26])[CH:8]=[C:9]([CH:11]=[CH:12][CH2:13][C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[OH:22])[CH:10]=1)=[O:5])[CH3:2]

Participants

3

Reactant 1

HCID 54057319HCID 54057319, compound

Product 1

HCID 53747219HCID 53747219, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1.00 g (2.79 mmol) of 2-ethoxycarbonyl-1-methyl-4-[2-(3-oxapropyloxy)-5-methoxyphenyl]propenylpyrrole in 5 ml of 1:1 aqueous trifluoroacetic acid was stirred at 0° for 1 hour, then at room temperature for 1 hour. The solution was partitioned between ether and water and the ether layer was washed with 3 portions of water. The ether extract was dried (Na2SO4), concentrated, and chromatographed on silica using 20% ethylacetatehexane to afford 0.68 g (77%) 2-ethoxycarbonyl-1-methyl-4-(2-hydroxy-5-methoxyphenyl)propenylpyrrole of a colorless glass. NMR (CDCl3) δ1.30 (t, 3H, J=6 Hz), 3.4 (trans), 3.65 (cis) (d, total 2H, J=6 Hz, trans:cis=10:1), 3.78 (s, 3H), 3.90 (s, 3H), 4.25 (q, 2H, J=6 Hz), 5.75-6.6 (m, 2H), 6.7-7.3 (m, 5H).

Workup

  1. customThe solution was partitioned between ether and water
  2. washthe ether layer was washed with 3 portions of water
  3. extractionThe ether extract
  4. dry with materialwas dried (Na2SO4)
  5. concentrationconcentrated
  6. customchromatographed on silica using 20% ethylacetatehexane

Sources & evidence

ORD record
ord-3968f90188d44d88b43223ca1fa64555
Source dataset
uspto-grants-1988_10
Patent number
US04778818

Reaction notes

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