methyl (2E)-3-[4-(1,3-dioxolan-2-yl)thiophen-2-yl]acrylate → methyl (2E)-3-(4-formylthiophen-2-yl)acrylate

HRID 1465499Notes

Reaction equation

HRID 1465499 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:7]=[C:8](/[CH:11]=[CH:12]/[C:13]([O:15][CH3:16])=[O:14])[S:9][CH:10]=1>C(O)(=O)C>[CH:2]([C:6]1[CH:7]=[C:8](/[CH:11]=[CH:12]/[C:13]([O:15][CH3:16])=[O:14])[S:9][CH:10]=1)=[O:1]

Participants

3

Reactant 1

HCID 58181286methyl (2E)-3-[4-(1,3-dioxolan-2-yl)thiophen-2-yl]acrylate

Product 1

HCID 86650009methyl (2E)-3-(4-formylthiophen-2-yl)acrylateYield 94.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
37.5 °C

Procedure

To methyl (2E)-3-[4-(1,3-dioxolan-2-yl)thiophen-2-yl]prop-2-enoate (2.200 g, 9.156 mmol) was added 50% acetic acid aqueous solution (22 ml), and the mixture was stirred at 35 to 40° C. for 2 hrs. The reaction mixture was concentrated under reduced pressure, and water (50 ml) was added. The mixture was concentrated again under reduced pressure, and water (100 ml) was added. The precipitate was collected by filtration, washed with water, and dried under reduced pressure to give methyl (2E)-3-(4-formylthiophen-2-yl)prop-2-enoate (1.701 g, yield 94.7%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and water (50 ml)
  2. additionwas added
  3. concentrationThe mixture was concentrated again under reduced pressure, and water (100 ml)
  4. additionwas added
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-42d07b38b59b4697a371269cc9629d7e
Source dataset
uspto-grants-2015_04
Patent number
US08999989B2

Reaction notes

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