HCID 21288120, compound → HCID 54057319, compound

HRID 1789006Notes

Reaction equation

HRID 1789006 reaction equation
[CH2:1]([Li])CCC.[I-].[CH2:7]([O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=1[CH2:19][CH2:20][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:8][OH:9].[CH2:40]([O:42][C:43]([C:45]1(C=O)[CH2:49][CH:48]=[CH:47][N:46]1[CH3:50])=[O:44])[CH3:41]>O1CCCC1>[CH2:40]([O:42][C:43]([C:45]1[N:46]([CH3:50])[CH:47]=[C:48]([CH:1]=[CH:20][CH2:19][C:12]2[CH:13]=[C:14]([O:17][CH3:18])[CH:15]=[CH:16][C:11]=2[O:10][CH2:7][CH2:8][OH:9])[CH:49]=1)=[O:44])[CH3:41]

Participants

5

Reactant 3

HCID 21288120HCID 21288120, compoundHCID 21288126HCID 21288126, compoundHCID 178418339Butyllithium

Product 1

HCID 54057319HCID 54057319, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.6M n-butyllithium (4.0 ml, 6.0 mmol) was added to a suspension of 3.45 g (5.90 mmol) of 2-[2-(3-oxapropyloxy)-5-methoxyphenyl]ethyltriphenylphosphonium iodide in 20 ml of dry tetrahydrofuran at 0°. After 30 minutes a solution of 1.10 g (6.07 mmol) of 2-ethoxycarbonyl-1-methylpyrrole-2-carboxaldehyde in 5 ml of dry tetrahydrofuran was added and the solution was stirred for 30 minutes. The mixture was partitioned between ether and water and the ether layer was washed with water, dried (Na2SO4) and evaporated. The residue was chromatographed on silica using 20% ethylacetatehexane to afford 1.78 g (85%) of 2-ethoxycarbonyl-1-methyl-4-[2-(3-oxapropyloxy)-5-methoxyphenyl]propenylpyrrole as a colorless glass.

Workup

  1. customThe mixture was partitioned between ether and water
  2. washthe ether layer was washed with water
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was chromatographed on silica using 20% ethylacetatehexane

Sources & evidence

ORD record
ord-c7319b78311f4d539f78823d48903e7b
Source dataset
uspto-grants-1987_08
Patent number
US04686235

Reaction notes

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