Benzyl Alcohol → 2-(Benzyloxy)nicotinonitrile

HRID 2395062Notes

Reaction equation

HRID 2395062 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[C:12]1[N:19]=[CH:18][CH:17]=[CH:16][C:13]=1[C:14]#[N:15].O>CCCCCC.C1COCC1>[CH2:3]([O:10][C:12]1[C:13]([C:14]#[N:15])=[CH:16][CH:17]=[CH:18][N:19]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 24758Sodium hydrideHCID 810792-Chloronicotinonitrile

Product 1

HCID 126045112-(Benzyloxy)nicotinonitrile

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

Sodium hydride (60%, 2.89 g, 72.3 mmol) was washed with hexane (1×) and suspended in THF (50 ml). Anhydrous benzyl alcohol (8.57 g, 79.3 mmol) was added dropwise and the reaction mixture was stirred for 30 minutes. A solution of 2-chloronicotinonitrile (10.0 g, 72.2 mmol) in THF (50 ml) was added via a syringe (exotherm). The reaction was stirred at ambient temperature for 18 hours then water was added to quench the reaction. The reaction mixture was partitioned between EtOAc/water and the organic phase dried (MgSO4) and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2) to give 2-benzyloxy-3-cyanopyridine as a pale yellow oil which crystallised on standing (11.4 g, 75%).

Workup

  1. stirringThe reaction was stirred at ambient temperature for 18 hours
  2. customto quench
  3. customthe reaction
  4. customThe reaction mixture was partitioned between EtOAc/water
  5. dry with materialthe organic phase dried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by chromatography (SiO2, CH2Cl2)

Sources & evidence

ORD record
ord-116737acd78f41219c2f0b2a87497f61
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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