HCID 21288120, compound → HCID 54057319, compound

HRID 868285Notes

Reaction equation

HRID 868285 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. NMR (CDCl3) δ1.30 (t, 3H, J=6 Hz), 3.40 (s, 3H), 3.45 (trans), 3.70 (cis) (d, J=6 Hz, total 2H, cis:trans, 1:10), 3.78 (s, 3H), 3.90 (s, 3H), 4.25 (q, 2H, J=6 Hz), 5.0 (trans), 5.05 (cis) (s, total 2H), 5.75-6.6 (m, 2H), 6.7-7.3 (m, 5H).

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-de82925a3b474ce6b2e1d5c4dac0c150
Source dataset
uspto-grants-1988_10
Patent number
US04778818

Reaction notes

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