Dimethylformamide dimethyl acetal → HCID 66876960, compound

HRID 1170452Notes

Reaction equation

HRID 1170452 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([CH2:6][C:7]([O:9][CH3:10])=[O:8])=[O:5].CO[CH:17](OC)[N:18]([CH3:20])[CH3:19]>>[Cl:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[C:4](=[O:5])[C:6](=[CH:17][N:18]([CH3:20])[CH3:19])[C:7]([O:9][CH3:10])=[O:8]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 735887methyl 3-(2-chlorophenyl)-3-oxopropanoate

Product 1

HCID 66876960HCID 66876960, compoundYield 57.7%

Procedure

A mixture of methyl 2-chlorobenzoylacetate (Acros; 266 mg, 1.25 mmol) and N,N-dimethylformamide dimethylacetal (161 mg, 1.35 mmol) was stirred at rt under N2 for 2 weeks. The reaction was then concentrated in vacuo and the residue was adsorbed on silica gel and chromatographed. Elution with 3:1 EtOAc/hexanes afforded 193 mg of the title compound as a yellow solid.

Workup

  1. concentrationThe reaction was then concentrated in vacuo
  2. customchromatographed
  3. washElution with 3:1 EtOAc/hexanes

Sources & evidence

ORD record
ord-074ac954192b479cbacf60b062e3b024
Source dataset
uspto-grants-2010_11
Patent number
US07825278B2

Reaction notes

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