Hydrochloric Acid → HCID 54703303, compound

HRID 1262815Notes

Reaction equation

HRID 1262815 reaction equation
[H-].[Na+].[C:3](OC(C)C)(=[O:7])[C:4]([CH3:6])=O.[S:12]([CH:21](O)[C:22]([O:24][CH:25]([CH3:27])[CH3:26])=[O:23])[CH:13](O)[C:14]([O:16][CH:17]([CH3:19])[CH3:18])=[O:15].Cl>C(O)(C)C>[CH3:6][C:4]1[C:3]([OH:7])=[C:21]([C:22]([O:24][CH:25]([CH3:27])[CH3:26])=[O:23])[S:12][C:13]=1[C:14]([O:16][CH:17]([CH3:19])[CH3:18])=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 9964097Isopropyl pyruvateHCID 20456125HCID 20456125, compound

Product 1

HCID 54703303HCID 54703303, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Sodium hydride (132 g, 5.52 mol) was added gradually into isopropyl alcohol (2-3 l) with cooling. To the resulting solution was then added a mixture of isopropyl pyruvate (360 g, 2.76 mol) and di-isopropyl 2,2'-thiodiglycolate (648 g, 2.76 mol) over 20-30 minutes with ice-cooling so that the solution was kept at 60°-80° C. The solution was stirred further for 2 hours at a temperature of 60°-40° C. The solution was poured into an ice-cooled dilute hydrochloric acid solution to form a white crystalline mass, which was recovered by filtration and then washed with water. It was recrystallized from methanol (3 l) to give pure di-isopropyl 3-methyl-4-hydroxy-2,5-thiophene-dicarboxylate (270 g, 34%), m.p. 87°-89° C.

Workup

  1. temperaturewith cooling
  2. additionTo the resulting solution was then added
  3. temperaturecooling so that the solution
  4. customwas kept at 60°-80° C
  5. customto form a white crystalline mass, which
  6. filtrationwas recovered by filtration
  7. washwashed with water
  8. customIt was recrystallized from methanol (3 l)

Sources & evidence

ORD record
ord-8e8c80cd7b4a4b91b445a34a2c92db4d
Source dataset
uspto-grants-1984_06
Patent number
US04454131

Reaction notes

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