Oxazole → HCID 18967676, compound

HRID 399476Notes

Reaction equation

HRID 399476 reaction equation
C([Li])CCC.[O:6]1[CH:10]=[CH:9][N:8]=[CH:7]1.[Cl:11][C:12]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:13]=1[CH:14]=[O:15].[Cl-].[NH4+]>C1COCC1>[Cl:11][C:12]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:13]=1[CH:14]([C:7]1[O:6][CH:10]=[CH:9][N:8]=1)[OH:15]

Participants

6

Reactant 4

HCID 9255OxazoleHCID 25517Ammonium ChlorideHCID 2781662-Chloro-4-nitrobenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 18967676HCID 18967676, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

n-Butyl lithium (1.6M in hexane, 7.4 ml) was added to a solution of oxazole (0.78 ml) in THF (100 ml) which had been cooled to -70° C. The mixture was stirred at that temperature for 1 hour. A solution of 2-chloro-4-nitrobenzaldehyde (2 g) in THF (5 ml) was added and the mixture was stirred at -70° C. for 3 hours. A saturated aqueous ammonium chloride solution was added and the mixture was extracted with ethyl acetate. The organic phase was dried (MgSO4) and evaporated to give 1-(2-chloro-4-nitrophenyl)-1-(2-oxazolyl)methanol (1.45 g), m.p. 158°-160° C.

Workup

  1. stirringthe mixture was stirred at -70° C. for 3 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-9a4dab682fce4eb6918016ceb75189d8
Source dataset
uspto-grants-1998_10
Patent number
US05821246

Reaction notes

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