Dimethyl malonate → HCID 19807159, compound

HRID 1681129Notes

Reaction equation

HRID 1681129 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[S:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH2:15]Cl>C1COCC1>[S:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH2:15][C:2]([CH2:15][C:11]1[S:10][CH:14]=[CH:13][CH:12]=1)([C:1]([O:8][CH3:9])=[O:7])[C:3]([O:5][CH3:6])=[O:4]

Participants

4

Reactant 2

HCID 7943Dimethyl malonateHCID 698302-(Chloromethyl)thiophene

Product 1

HCID 19807159HCID 19807159, compoundYield 16.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

87.8 g of dimethyl malonate and 41.0 g of potassium t-butylate are dissolved in 1.1 l of THF (anhydrous) while cooling in ice, and, under argon, 44.1 g of 2-thienylmethylchloride in 500 ml of THF are added dropwise. The mixture is stirred at R.T. for 3 h, the KCL is removed by filtration, the solvent is removed in vacuo, and the residue is chromatographed. 33.8 g of the title compound (I) are obtained as a colorless oil, in addition to 8.8 g of dimethyl bis-(2-thienylmethyl)malonate (II)

Workup

  1. temperaturewhile cooling in ice
  2. customthe KCL is removed by filtration
  3. customthe solvent is removed in vacuo
  4. customthe residue is chromatographed

Sources & evidence

ORD record
ord-55b4cd9faad74e5caabfd13c4b6e7f06
Source dataset
uspto-grants-1992_12
Patent number
US05169841

Reaction notes

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