Water → HCID 23503279, compound

HRID 1835138Notes

Reaction equation

HRID 1835138 reaction equation
C([N-]C(C)C)(C)C.[Li+].[S:9]1[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10]1.[CH:17](=[O:22])[CH2:18][CH:19]([CH3:21])[CH3:20].O>O1CCCC1>[CH3:20][CH:19]([CH3:21])[CH2:18][C:17]([C:10]1[S:9][CH:13]=[CH:12][C:11]=1[C:14]([OH:16])=[O:15])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 6918Thiophene-3-carboxylic acidHCID 115523-MethylbutanalHCID 2724682Lithium diisopropylamide

Product 1

HCID 23503279HCID 23503279, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
25 °C

Procedure

Lithium diisopropylamide (86 mmol) in tetrahydrofuran (30 ml) was added at 0° C. to a solution of thiophene-3-carboxylic acid (5 g) in tetrahydrofuran (50 ml). Isovaleraldehyde (4.6 ml) was added as a solution in tetrahydrofuran (30 ml) at 0° C. The reaction mixture was stirred at 25° C. for 3 hours and then water (100 ml) was added and the tetrahydrofuran was removed in vacuo. The aqueous residue obtained was extracted with ethyl acetate and the aqueous phase added to potassium permanganate (12.3 g) and warmed to 60° C. for 1.5 hours. The mixture was filtered, allowed to cool to ambient temperature, and then acidified with dilute hydrochloric acid. The acidic aqueous mixture was extracted with ethyl acetate and the organic extract dried and evaporated to give the sub-title compound as an oil (5.3 g).

Workup

  1. customthe tetrahydrofuran was removed in vacuo
  2. customThe aqueous residue obtained
  3. extractionwas extracted with ethyl acetate
  4. additionthe aqueous phase added to potassium permanganate (12.3 g)
  5. temperaturewarmed to 60° C. for 1.5 hours
  6. filtrationThe mixture was filtered
  7. temperatureto cool to ambient temperature
  8. extractionThe acidic aqueous mixture was extracted with ethyl acetate
  9. extractionthe organic extract
  10. customdried
  11. customevaporated

Sources & evidence

ORD record
ord-9083b6b6b6a2494e9a53316296c1c90f
Source dataset
uspto-grants-2004_08
Patent number
US06770646B2

Reaction notes

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