Benzyl Alcohol → 6-(Benzyloxy)pyridine-3-carbonitrile

HRID 1991415Notes

Reaction equation

HRID 1991415 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.[CH2:10]([OH:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[H-].[Na+].C(OC(=O)C)C.O>C1COCC1>[CH2:10]([O:17][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 22728543Water ethylacetate

Product 1

HCID 247001066-(Benzyloxy)pyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

20 mmol of 6-Chloro-nicotinonitrile were dissolved in THF. 1.1 eq. of benzyl alcohol were added. The reaction mixture was cooled to 0° C. and flushed with argon. 4 eq of NaH were added slowly. After 15 min the product was isolated via extraction from ethylacetate/water.

Workup

  1. customflushed with argon

Sources & evidence

ORD record
ord-3b87310e94714395b9e6b08ddc99d610
Source dataset
uspto-grants-2010_01
Patent number
US07645776B2

Reaction notes

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