5-[(Dimethylamino)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione → HCID 12173656, compound

HRID 1711979Notes

Reaction equation

HRID 1711979 reaction equation
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.CN([CH:9]=[C:10]1[C:15](=[O:16])[O:14][C:13]([CH3:18])([CH3:17])[O:12][C:11]1=[O:19])C>O1CCCC1>[CH:1]1([CH:9]=[C:10]2[C:11](=[O:19])[O:12][C:13]([CH3:17])([CH3:18])[O:14][C:15]2=[O:16])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 27511565-[(Dimethylamino)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dioneHCID 178418630HCID 178418630, compound

Product 1

HCID 12173656HCID 12173656, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 0.5 M solution (13 ml, 6.6 mmol) of cyclopropylmagnesiumbromide in tetrahydrofuran was added dropwise to a solution of 5-dimethylaminomethylene-2,2-dimethyl-1,3-dioxane-4,6-dione (1.0 g, 5.0 mmol) in tetrahydrofuran (12 ml) at 23° C. After stirring the mixture for 1 hr, the reaction solution was quenched with saturated aqueous ammonium chloride solution. The organic layer was separated and the water layer was extracted with dichloromethane. The combined organic layers were washed with water and brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (hexane/EtOAc 5:1) followed by crystallization from hexane to give 498 mg of the pure title product as a pale yellow powder. (yield: 51%)

Workup

  1. customthe reaction solution was quenched with saturated aqueous ammonium chloride solution
  2. customThe organic layer was separated
  3. extractionthe water layer was extracted with dichloromethane
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (hexane/EtOAc 5:1)
  8. customfollowed by crystallization from hexane

Sources & evidence

ORD record
ord-090503ec12594f49948a4632eae41bca
Source dataset
uspto-grants-2010_09
Patent number
US07790882B2

Reaction notes

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