Dimethylformamide → Methyl 3-cyano-5,6,7,8-tetrahydro-1-naphthalenecarboxylate

HRID 2185887Notes

Reaction equation

HRID 2185887 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]([C:17]([O:19][CH3:20])=[O:18])[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:15]=2[CH:16]=1)(=O)=O.[CH3:23][N:24](C=O)C>C([O-])(O)=O.[Na+].[C-]#N.[Zn+2].[C-]#N>[C:23]([C:7]1[CH:8]=[C:9]([C:17]([O:19][CH3:20])=[O:18])[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:15]=2[CH:16]=1)#[N:24]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 22452647Methyl 3-trifluoromethylsulfonyloxy-5,6,7,8-tetrahydro-1-naphthalenecarboxylate

Product 1

HCID 22452655Methyl 3-cyano-5,6,7,8-tetrahydro-1-naphthalenecarboxylateYield 73%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of methyl 3-trifluoromethylsulfonyloxy-5,6,7,8-tetrahydro-1-naphthalenecarboxylate (2.08 g, 6.15 mmol), zinc cyanide (0.81 g, 6.89 mmol) and tetrakistriphenylphosphine palladium (0.56 g, 0.48 mmol) in DMF (8 mL) was stirred at 120° C. for 1 h. The mixture was diluted with saturated NaHCO3, extracted with EtOAc, dried (MgSO4), filtered, and concentrated. Following column chromatography methyl-3-cyano-5,6,7,8-tetrahydro-1-naphthalenecarboxylate was obtained as a white solid (960 mg, 73%). 1H NMR (CDCl3) δ 7.94 (s, 1H), 7.49 (s, 1H), 3.90 (s, 3H), 3.11 (s, 2H), 2.84 (s, 2H), 1.81 (m, 4H); MS m/z 216.1 (M+H), 214.1 (M−H).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-535c189727084ce0a79d5619404326d9
Source dataset
uspto-grants-2002_06
Patent number
US06403601B1

Reaction notes

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