Oxalyl chloride → HCID 54092213, compound

HRID 343751Notes

Reaction equation

HRID 343751 reaction equation
C1(C(=O)CC(OC(C)(C)C)=O)CC1.[O-]CC.[Mg+2].[O-]CC.[CH3:21][C:22]1[C:30]([O:31][CH2:32][CH3:33])=[C:29]([S:34]([CH3:37])(=[O:36])=[O:35])[CH:28]=[CH:27][C:23]=1[C:24](O)=[O:25].C(Cl)(=O)C([Cl:41])=O>C(OCC)C>[CH3:21][C:22]1[C:30]([O:31][CH2:32][CH3:33])=[C:29]([S:34]([CH3:37])(=[O:36])=[O:35])[CH:28]=[CH:27][C:23]=1[C:24]([Cl:41])=[O:25]

Participants

6

Reactant 4

HCID 65578Oxalyl chlorideHCID 164963Magnesium ethanolateHCID 11126948Tert-butyl 3-cyclopropyl-3-oxopropanoateHCID 53707224HCID 53707224, compound

Product 1

HCID 54092213HCID 54092213, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of tert-butyl 3-cyclopropyl-3-oxopropionate (9.2 g) in ethyl ether (200 mL) was added magnesium ethoxide (5.7 g). The reaction mixture was heated at reflux for 1 hour. After cooling back to room temperature, a solution of 2-methyl-3-ethoxy-4-methylsulfonylbenzoyl chloride (13.8 g), which was prepared from 2-methyl-3-ethoxy-4-methylsulfonylbenzoic acid (the preparation of which is described in U.S. Pat. No. 5,329,041 which is incorporated herein by reference) and oxalyl chloride, in ethyl ether (50 mL) was added over a period of 15 minutes. After stirring overnight at room temperature, the reaction mixture was poured over ice-water (100 mL), and the phases were separated. The ether layer was dried over magnesium sulfate and then concentrated in vacuo to afford 17 g of the crude product as an oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1 hour
  3. customthe preparation of which
  4. customthe phases were separated
  5. dry with materialThe ether layer was dried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cfd0d35d4f4547678d9761b3c7e7f5d1
Source dataset
uspto-grants-1999_01
Patent number
US05863865

Reaction notes

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