Water → HCID 18953967, compound

HRID 2255245Notes

Reaction equation

HRID 2255245 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH2:13][CH2:14][CH2:15][OH:16])[O:11][CH:12]=2)=[CH:4][CH:3]=1.[H-].[Na+].O>CN(C=O)C.C(Br)C1C=CC=CC=1>[CH2:8]([O:16][CH2:15][CH2:14][CH2:13][C:10]1[O:11][CH:12]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[N:9]=1)[C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 9837611HCID 9837611, compound

Product 1

HCID 18953967HCID 18953967, compoundYield 123.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 7498Benzyl BromideSolvent

Procedure

To a solution of 3-[4-(4-chlorophenyl)-2-oxazolyl]propanol (0.6 g) in DMF (10 ml) were added 60% (W/W) sodium hydride in oil (0.12 g) and benzyl bromide (0.3 ml), followed by stirring for 3 hours at room temperature. After additional stirring for an hour at 30° C., the reaction mixture was poured into water and then extracted with ether. The ether layer was washed with water, dried over MgSO4 and distilled to remove the solvent. The oily residue was subjected to a silica gel column chromatography. Oily 3-[4-(4-chlorophenyl)-2-oxazoly]propyl benzyl ether (0.512 g, 62%) was obtained from the fraction eluted with ether-hexane (1:4, V/V).

Workup

  1. stirringAfter additional stirring for an hour at 30° C.
  2. extractionextracted with ether
  3. washThe ether layer was washed with water
  4. dry with materialdried over MgSO4
  5. distillationdistilled
  6. customto remove the solvent

Sources & evidence

ORD record
ord-824e00fe383c45a9b8245591583a18ed
Source dataset
uspto-grants-1993_08
Patent number
US05239080

Reaction notes

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