Sodium Hydroxide → HCID 58495688, compound

HRID 1190996Notes

Reaction equation

HRID 1190996 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1(/[CH:13]=[CH:14]\[C:15]2[CH:16]=[CH:17][C:18]([C:21]#[N:22])=[N:19][CH:20]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[OH-].[Na+]>C1COCC1.O.C(OCC)C>[NH2:22][CH2:21][C:18]1[CH:17]=[CH:16][C:15](/[CH:14]=[CH:13]\[CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)=[CH:20][N:19]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 58495654HCID 58495654, compound

Product 1

HCID 58495688HCID 58495688, compoundYield 130.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, add lithium aluminum hydride (965 mg, 25.4 mmol) to THF (20 mL) at 0° C. Add a solution of (Z)-5-(2-cyclohexylvinyl)-pyridine-2-carbonitrile (1.8 g, 1.74 mmol) in THF (5 mL) and stir at 0° C. for 1 h and to room temperature overnight. Cool the mixture to 0° C. and carefully add water (0.95 mL). Add diethyl ether (125 mL), 3N aqueous NaOH (0.95 mL), and water (2.85 mL) and stir for 1 h at room temperature. Filter the solid residue and concentrate in vacuo to obtain the title compound as a colorless oil (0.49 g, 30%). MS (APCI+) m/z: 217 (M+H)+.

Workup

  1. temperatureCool the mixture to 0° C.
  2. filtrationFilter the solid residue
  3. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-f50aa6ff82fb403d9cbd7f9003e4dbd8
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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