Ethyl Glycolate → HCID 57928066, compound

HRID 657092Notes

Reaction equation

HRID 657092 reaction equation
[N+](=[C:3]([C:8]([O:10][CH3:11])=[O:9])[C:4]([O:6][CH3:7])=[O:5])=[N-].[C:12]([O:16][CH2:17][CH3:18])(=[O:15])[CH2:13][OH:14]>C(Cl)Cl.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:17]([O:16][C:12](=[O:15])[CH2:13][O:14][CH:3]([C:8]([O:10][CH3:11])=[O:9])[C:4]([O:6][CH3:7])=[O:5])[CH3:18]

Participants

5

Reactant 2

HCID 12184Ethyl GlycolateHCID 5476732-Diazonio-1,3-dimethoxy-3-oxoprop-1-en-1-olate

Product 1

HCID 57928066HCID 57928066, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 423677Acetic acid, rhodium salt (4:2)CatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of dimethyl diazopropanedioate (4 g, 25 mmol), prepared according to Peace, Carman, Wulfman, Synthesis, 658-661, (1971), in DCM (10 mL) was added ethyl glycolate (1.2 mL, 12.8 mmol) followed by rhodium (II) acetate dimer (2 g, 20% mol). The reaction mixture was stirred at room temperature for 24 h. The resulting suspension was filtered through a pad of Celite® and the solvent was removed in vacuo. The crude residue was purified by column chromatography (silica gel) using a 0-60% EtOAc/hexanes gradient to provide the desired product as an oil (3 g, 97%).

Workup

  1. filtrationThe resulting suspension was filtered through a pad of Celite®
  2. customthe solvent was removed in vacuo
  3. customThe crude residue was purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-9da16bfca58047a892606f3095c01306
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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