Diethyl Ether → HCID 54329809, compound

HRID 982403Notes

Reaction equation

HRID 982403 reaction equation
[CH2:1]1[C:6](=[O:7])[O:5][CH2:4][C:2]1=[O:3].[I:8][C:9]1[S:13][C:12]([CH:14]=O)=[CH:11][CH:10]=1.C1COCC1.CCOCC>O>[I:8][C:9]1[S:13][C:12]([CH:14]=[C:1]2[C:2](=[O:3])[CH2:4][O:5][C:6]2=[O:7])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 521261Tetronic acidHCID 30143612-Thiophenecarboxaldehyde, 5-iodo-

Product 1

HCID 54329809HCID 54329809, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.59 gm of tetronic acid (FW=100, 0.056 mole) and 3.65 gm of 5-iodo-2-thiophenecarboxaldehyde (FW=238, 15.3 mmole) were added to a 25 mL roundbottom flask and 2.5 mL of THF were added and the solution was stirred for five minutes. The sludge was allowed to react for 30 minutes, occasionally helping the stirring with a glass rod. The precipitate was then treated with 10 mL of ether and 10 mL of water and swirled. The yellow crystals were then collected on a buchner funnel, washing them with ether, water and ether again. The excess 5-iodo-2-thiophenecarboxaldehyde was then recovered by extracting to aqueous layer with ether and resublimed. The crude adduct was dissolved in hot CHCl3 (approximately 250 mL) and passed through a silica plug (approximately 5 cm). The crystals obtained after solvent evaporation were recrystallized from ethyl acetate/igroin and the yield was 0.85 gm (46%). The material melted at 211°-212° C. (dec.) C9H6IO3S: %C 33.77; %H 1.57; found %C 33.53; %H 1.83 NMR results: 1HNMR (d6DMSO,(H20)/TMS) 6 4.69 (2H, d, 4.8 Hz); 7.53 (1H, m); 8.08 (1H, m).

Workup

  1. customto react for 30 minutes
  2. customThe yellow crystals were then collected on a buchner funnel
  3. washwashing them with ether, water and ether again
  4. customThe excess 5-iodo-2-thiophenecarboxaldehyde was then recovered
  5. extractionby extracting to aqueous layer with ether
  6. dissolutionThe crude adduct was dissolved in hot CHCl3 (approximately 250 mL)
  7. customThe crystals obtained
  8. customafter solvent evaporation
  9. customwere recrystallized from ethyl acetate/igroin
  10. custom%H 1.83 NMR results

Sources & evidence

ORD record
ord-6fd3ec56bc82430da89479b7352fb230
Source dataset
uspto-grants-1991_02
Patent number
US04996227

Reaction notes

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