Dimethylformamide → HCID 458299, compound

HRID 2299103Notes

Reaction equation

HRID 2299103 reaction equation
[OH2:1].[OH-:2].[Li+].C(OC)(=O)[CH2:5][SH:6].[C:10]([O:15][CH2:16][CH3:17])(=O)/[CH:11]=[CH:12]/[CH3:13].[CH3:18]N(C=O)C>C(OCC)(=O)C>[O:1]=[C:12]1[CH:13]([CH3:18])[S:6][CH2:5][CH:11]1[C:10]([O:15][CH2:16][CH3:17])=[O:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 16907Methyl ThioglycolateHCID 168937Lithium hydroxide, monohydrateHCID 429065Ethyl trans-crotonate

Product 1

HCID 458299HCID 458299, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Lithium hydroxide hydrate (3.48 g, 82.9 mmol) was added slowly to a solution of methyl thioglycolate (4.0 g, 37.7 mmol) and ethyl crotonate (4.3 g, 37.7 mmol) in DMF (60 mL), cooled to 0° C. The reaction was allowed to warm to room temperature, stir for 18 h, taken up in ethyl acetate, washed with 1 N HCl (until they remained acidic), washed with water, brine, dried over magnesium sulfate and concentrated in vacuo to give the ethyl 4-oxotetrahydro-5-methyl-3-thiophenecarboxylate (6.76 g, 100%) as an oil.

Workup

  1. temperatureto warm to room temperature
  2. washwashed with 1 N HCl (until they remained acidic)
  3. washwashed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2f8fbc50e7304c98b7960e29adf959de
Source dataset
uspto-grants-2002_12
Patent number
US06495565B2

Reaction notes

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