Acetonitrile → HCID 86590510, compound

HRID 1696918Notes

Reaction equation

HRID 1696918 reaction equation
[K].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6]CC)=O.[Cl-:13].[Mg+2].[Cl-:15].C([N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])C.[C:23](#N)[CH3:24]>>[Cl:13][C:21]1[C:22]([C:4](=[O:6])[CH2:3][C:2]([O:10][CH2:11][CH3:12])=[O:9])=[C:23]([CH3:24])[CH:20]=[C:19]([Cl:15])[N:18]=1

Participants

6

Reactant 5

HCID 6342AcetonitrileHCID 7761Diethyl MalonateHCID 8471TriethylamineHCID 5360315Magnesium ChlorideHCID 5462222Potassium

Product 1

HCID 86590510HCID 86590510, compound

Procedure

A solution of EXAMPLE 65A (4.07 g) and oxalyl chloride (1.82 mL) in dichloromethane (80 mL) was treated with N,N-dimethylformamide (0.0459 mL), stirred for 2 hours, concentrated, and dissolved in dichloromethane (30 mL) to provide an acid chloride solution. A suspension of the potassium salt of diethyl malonate (8.41 g) in acetonitrile (80 mL) at 0° C. was treated with magnesium chloride (6.58 g) and triethylamine (6.88 mL), warmed to ambient temperature, stirred for three hours, treated with the acid chloride solution, stirred for 1 hour, and concentrated. The concentrate was treated with 1M HCl (100 mL) and extracted with ethyl acetate. The extract was washed with 1M HCl, saturated sodium bicarbonate and brine, dried (MgSO4), filtered, and concentrated; and the concentrate was flash chromatographed on silica gel with 25% ethyl acetate/hexanes.

Workup

  1. stirringstirred for 1 hour
  2. concentrationconcentrated
  3. additionThe concentrate was treated with 1M HCl (100 mL)
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with 1M HCl, saturated sodium bicarbonate and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customchromatographed on silica gel with 25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-d8a3faefb1f34c56a403ea35731b9250
Source dataset
uspto-grants-2012_04
Patent number
US08163769B2

Reaction notes

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