Dimethylformamide → HCID 23001103, compound

HRID 397621Notes

Reaction equation

HRID 397621 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]1[CH:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:12]1[CH2:11][CH2:10]2)(=O)=O.[CH3:25][N:26](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:25]([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]1[CH:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:12]1[CH2:11][CH2:10]2)#[N:26]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 23001120HCID 23001120, compound

Product 1

HCID 23001103HCID 23001103, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

Ethyl 5-{[(trifluoromethyl)sulfonyl]oxy}-1a,2,3,7b-tetrahydro-1H-cyclopropa[a]naphthalene-1-carboxylate (0.2 g, 0.5 mmol) was mixed with Zn(CN)2 (0.82 mmol) and Pd(Ph3P)4 (56 mg, 10 mol %) in DMF (4 ml), bubbled with argon for 5 min and heated at stirring in a closed vial for 14 h at 100° C. Reaction was monitored by GC. The reaction mixture was concentrated by rotary evaporation, mixed with saturated NH4Cl and extracted into ethylacetate (3×15 ml). Organic extract was washed with water and brine, dried under Na2SO4. Concentration gave 0.12 g of product as an oil (yield 90%).

Workup

  1. custombubbled with argon for 5 min
  2. temperatureheated
  3. customReaction
  4. concentrationThe reaction mixture was concentrated by rotary evaporation
  5. additionmixed with saturated NH4Cl
  6. extractionextracted into ethylacetate (3×15 ml)
  7. extractionOrganic extract
  8. washwas washed with water and brine
  9. customdried under Na2SO4
  10. concentrationConcentration

Sources & evidence

ORD record
ord-b5c9ace153c4456fabea506c47bab6b7
Source dataset
uspto-grants-2003_08
Patent number
US06610714B2

Reaction notes

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