Dichloromethane → HCID 67349699, compound

HRID 1670727Notes

Reaction equation

HRID 1670727 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]([CH3:15])([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.ClCCl.[CH3:25][N:26](C)C(=O)C>[C-]#N.[Zn+2].[C-]#N.[Zn].C(OCC)(=O)C>[C:25]([C:2]1[N:7]=[CH:6][C:5]([CH:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]([CH3:15])([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1)#[N:26]

Participants

7

Reactant 3

HCID 6344DichloromethaneHCID 31374DimethylacetamideHCID 59138592HCID 59138592, compound

Product 1

HCID 67349699HCID 67349699, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of methyl 3-(6-chloropyridin-3-yl)-2,2-dimethyl-3-phenylpropanoate (0.11 g, 0.38 mmol), zinc cyanide (45 mg, 0.38 mmol), zinc (5 mg, 0.08 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (14 mg, 0.019 mmol), and N,N-dimethylacetamide (0.5 mL) was stirred at 120° C. under argon for 2 hr. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between saturated aqueous sodium bicarbonate solution (10 mL) and ethyl acetate (20 mL). The aqueous layer was separated and extracted with ethyl acetate (10 mL). The combined organic solutions were dried (Na2SO4) and concentrated. Silica gel flash chromatography (0-100% ethyl acetate in hexanes) gave methyl 3-(6-cyanopyridin-3-yl)-2,2-dimethyl-3-phenylpropanoate (70 mg, 0.24 mmol, 63% yield) as a colorless solid. MS found: (M+H)+=295.27.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between saturated aqueous sodium bicarbonate solution (10 mL) and ethyl acetate (20 mL)
  3. customThe aqueous layer was separated
  4. extractionextracted with ethyl acetate (10 mL)
  5. dry with materialThe combined organic solutions were dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7709619687e740abb2035214d5688697
Source dataset
uspto-grants-2011_08
Patent number
US07994190B2

Reaction notes

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