Potassium Carbonate → HCID 68701987, compound

HRID 646235Notes

Reaction equation

HRID 646235 reaction equation
C([O:3][C:4](=[O:16])[C:5]([C:7]1[S:8][C:9]([CH2:12][CH2:13][CH2:14][CH3:15])=[CH:10][CH:11]=1)=[O:6])C.C([O-])([O-])=O.[K+].[K+]>C(O)C>[CH2:12]([C:9]1[S:8][C:7]([C:5](=[O:6])[C:4]([OH:16])=[O:3])=[CH:11][CH:10]=1)[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 68697356Ethyl 5-butyl-α-oxo-2-thiopheneacetate

Product 1

HCID 68701987HCID 68701987, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To solution containing (5-butyl-thiophen-2-yl)-oxo-acetic acid ethyl ester (Step a, 1 g, 4.2 mmol) dissolved in ethanol 10 mL) was added K2CO3 2N (10 mL). The reaction was stirred at room temperature 6 h. The ethanol was removed under reduce pressure and the residue taken in water (50 mL) then washed with ether. The aqueous was separated and made acidic with concentrated HCl then extracted with CHCl3 (2×). The organic layers were separated and combined and dried over MgSO4, then filtered and stripped. A white solid (0.6 g, 67% yield) was recovered. MS m/e 211 (M)−; 1HNMR (DMSO-d6 300 MHz) δ 0.9 (t, 3H), 1.3 (m, 2H), 1.6 (m, 2H), 2.8 (t, 2H), 4.3 (b, 1H), 7.1 (s, 1H), 7.9 (s, 1H).

Workup

  1. customThe ethanol was removed
  2. washthen washed with ether
  3. customThe aqueous was separated
  4. extractionthen extracted with CHCl3 (2×)
  5. customThe organic layers were separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered

Sources & evidence

ORD record
ord-595c5fae69ad432fa203e77e20a7bdd7
Source dataset
uspto-grants-2010_04
Patent number
US07705030B2

Reaction notes

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