Water → tert-Butyl 5-formylthiophene-2-carboxylate

HRID 431504Notes

Reaction equation

HRID 431504 reaction equation
[C:1]([O:5][C:6]([C:8]1[S:9][C:10]([CH:13]2N(C)CCN2C)=[CH:11][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CI.[OH2:22]>C(OCC)C>[C:1]([O:5][C:6]([C:8]1[S:9][C:10]([CH:13]=[O:22])=[CH:11][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6328Methyl iodideHCID 54215656HCID 54215656, compound

Product 1

HCID 21473735tert-Butyl 5-formylthiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

2.54 g (9 mmol) of 5-(1,3-dimethyl-imidazolidin-2-yl)-thiophene-2-carboxylic acid tert-butyl ester wered dissolved in 15 ml of diethyl ether, and after addition of 5 ml of methyl iodide the solution was stirred overnight at room temperature. The resulting crystalline suspension was vigorously stirred for 1 hour with 100 ml water. Then 100 ml diethyl ether were added, and after separation of the phases the organic phase was dried with anhydrous magnesium sulfate. After filtration, the solvents were removed in vacuo. 1.7 g of a light brown oil were isolated which was sufficiently pure for use in the subsequent step.

Workup

  1. customafter separation of the phases the organic phase
  2. dry with materialwas dried with anhydrous magnesium sulfate
  3. filtrationAfter filtration
  4. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-579161f30bd4484ea55101b69e64c697
Source dataset
uspto-grants-2003_12
Patent number
US06660728B2

Reaction notes

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