3-Bromotoluene → HCID 22101820, compound

HRID 1458219Notes

Reaction equation

HRID 1458219 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[C:9]([CH3:13])[CH:10]=[CH:11][CH:12]=1.[CH3:14][C:15]1[N:16]=[CH:17][O:18][C:19]=1[CH:20]=[O:21].C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:14][C:15]1[N:16]=[CH:17][O:18][C:19]=1[CH:20]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[CH:8]=1)[OH:21]

Participants

6

Reactant 4

HCID 115603-BromotolueneHCID 516892Sodium BicarbonateHCID 149205234-Methyl-1,3-oxazole-5-carbaldehydeHCID 178418339Butyllithium

Product 1

HCID 22101820HCID 22101820, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyllithium (2.5 solution in hexanes, 3.9 ml) was added dropwise to a stirred solution of 3-bromotoluene (1.1 ml) in dry tetrahydrofuran (20 ml) at -70° C. under an atmosphere of dry nitrogen. After 20 minutes, 4-methyl-5-oxazolecarbaldehyde (1.15 g) in tetrahydrofuran (10 ml) was added. After 1 hour the mixture was allowed to warm to room temperature and was then heated under reflux for 1 hour. The cooled solution was poured into saturated aqueous sodium hydrogen carbonate. Extraction with ethyl acetate and flash chromatography then gave the title compound. M.p. 76.5°-77.5° C.

Workup

  1. waitAfter 1 hour the mixture was allowed
  2. temperaturewas then heated
  3. temperatureunder reflux for 1 hour
  4. extractionExtraction with ethyl acetate and flash chromatography

Sources & evidence

ORD record
ord-5429c46fb8fa4396a422c03afe35dafa
Source dataset
uspto-grants-1998_12
Patent number
US05849921

Reaction notes

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