Carbon Dioxide → HCID 178513892, compound

HRID 371120Notes

Reaction equation

HRID 371120 reaction equation
C([C:4]([Cl:11])=[CH:5][CH2:6][C:7]([O:9]C)=[S:8])(O)=O.C([N-:15][CH:16](C)C)(C)C.[Li+].C(=O)=[O:21].O>C1COCC1>[C:16]([CH:6]([CH:5]=[CH:4][Cl:11])[C:7]([OH:9])=[S:8])(=[O:21])[NH2:15]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 962WaterHCID 2724682Lithium diisopropylamideHCID 54059155HCID 54059155, compound

Product 1

HCID 178513892HCID 178513892, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl (2-chlorovinyl)thioacetate (1) (2 g) and lithium diisopropylamide (1.08 g) are stirred in THF (2 ml) at -60° C. for 15 minutes. After addition of dry ice (5 g), the mixture is stirred for 30 minutes and allowed to warm to room temperature. The reaction mixture is poured into water and washed with ethyl acetate to remove neutral material. The remaining aqueous solution is acidified with HCl and extracted with ethyl acetate. The extract is washed with water and vacuum evaporated to give the desired malonic acid ester (2). Yield: 747 mg.

Workup

  1. washwashed with ethyl acetate
  2. customto remove neutral material
  3. extractionextracted with ethyl acetate
  4. washThe extract is washed with water and vacuum
  5. customevaporated

Sources & evidence

ORD record
ord-63f0efd773ce4963bf5258df52f0494b
Source dataset
uspto-grants-1985_07
Patent number
US04529721

Reaction notes

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