Benzyl Alcohol → HCID 68957422, compound

HRID 1455637Notes

Reaction equation

HRID 1455637 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:12]1[C:17]([C:18]2[O:22][N:21]=[C:20]([CH3:23])[N:19]=2)=[CH:16][CH:15]=[CH:14][N:13]=1>CN(C=O)C.CCOCC.O>[CH2:1]([O:8][C:12]1[C:17]([C:18]2[O:22][N:21]=[C:20]([CH3:23])[N:19]=2)=[CH:16][CH:15]=[CH:14][N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 80272052-Chloro-3-(3-methyl-1,2,4-oxadiazol-5-yl)pyridine

Product 1

HCID 68957422HCID 68957422, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
20 °C

Procedure

To a solution of benzyl alcohol (1.5 eq) in DMF (0.4M) was added NaH (1.5 eq, 60%) followed by 2-chloro-3-(3-methyl-1,2,4-oxadiazol-5-yl)pyridine (1 eq) in DMF (0.5M) after 30 min.). The reaction was stirred at 20° C. for 1 h, diluted with Et2O and water. The organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. Flash chromatography (Hex:EtOAc; 80:20) afforded the title compound.

Workup

  1. washThe organic extracts were washed with brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-46a2a531b575456e90db0d2c2b29cfe1
Source dataset
uspto-grants-2009_01
Patent number
US07482456B2

Reaction notes

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