Benzyl Alcohol → HCID 54374393, compound

HRID 1387213Notes

Reaction equation

HRID 1387213 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[H][H].[CH3:13][CH:14]([C:16]1[N:17]=[C:18]([C:24]2[C:29](F)=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:31])[O:19][C:20]=1[O:21][CH2:22][CH3:23])[CH3:15]>CN(C=O)C>[CH3:13][CH:14]([C:16]1[N:17]=[C:18]([C:24]2[C:25]([Cl:31])=[CH:26][CH:27]=[CH:28][C:29]=2[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[O:19][C:20]=1[O:21][CH2:22][CH3:23])[CH3:15]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 54071069HCID 54071069, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54374393HCID 54374393, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

To 20 ml DMF solution containing 0.39 g benzyl alcohol, was added 60% sodium hydride in an amount of 0.16 g. After the end of hydrogen gas generation, DMF solution containing 1.0 g 4-(2-propyl)-5-ethoxy-2-(chloro-6-fluorophenyl)oxazole was added to the solution while keeping at −10° C. The solution reacted was heated up to 70° C. and then stirred for 5 hours. After completing the reaction, the solution reacted was poured into ice water and then extracted with ethyl acetate. The organic layer obtained was washed with water and saturated saline solution in turn, then dried by using anhydrous magnesium sulfate, and the solvent used was removed by distillation under reduced pressure. The residue obtained was purified by using silica gel column chromatography, affording the objective substance in an amount of 0.82 g.

Workup

  1. additionwas added to the solution
  2. customwhile keeping at −10° C
  3. customThe solution reacted
  4. customthe reaction
  5. customthe solution reacted
  6. extractionextracted with ethyl acetate
  7. customThe organic layer obtained
  8. washwas washed with water and saturated saline solution in turn
  9. customdried
  10. customthe solvent used was removed by distillation under reduced pressure
  11. customThe residue obtained
  12. customwas purified
  13. customaffording the objective substance in an amount of 0.82 g

Sources & evidence

ORD record
ord-afe30368983742baad91004df14d71c0
Source dataset
uspto-grants-2001_07
Patent number
US06268310B1

Reaction notes

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