Water → HCID 21840248, compound

HRID 1739042Notes

Reaction equation

HRID 1739042 reaction equation
[Cl-].[CH3:2][C:3]1[O:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:5][C:4]=1[CH2:14][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[O-]CC.[Na+].[Br:38][C:39]1[CH:46]=[CH:45][C:42]([CH:43]=O)=[CH:41][CH:40]=1.O>C(O)C>[Br:38][C:39]1[CH:46]=[CH:45][C:42](/[CH:43]=[CH:14]/[C:4]2[N:5]=[C:6]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[O:7][C:3]=2[CH3:2])=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 962WaterHCID 707414-BromobenzaldehydeHCID 2723922Sodium ethoxideHCID 21840259HCID 21840259, compound

Product 1

HCID 21840248HCID 21840248, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(5-Methyl-2-phenyl-4-oxazolylmethyl)triphenyl-phosphonium chloride (25.4 g) was added to a solution of sodium ethoxide in ethanol [prepared from sodium (1.4 g) and ethanol (300 ml)] under cooling. The mixture was stirred at room temperature for 5 minutes, and then 4-bromobenzaldehyde (10.0 g) was added. After stirring at room temperature for 2 hours, the reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel. The fractions eluted with ether-hexane (1:20, v/v) gave (E)-4-[2-(4-bromophenyl)vinyl]-5-methyl-2-phenyloxazole (13.1 g, 71%). This product was recrystallized from ethyl acetate-hexane. Colorless prisms, mp: 138-139° C.

Workup

  1. temperatureunder cooling
  2. stirringAfter stirring at room temperature for 2 hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washThe fractions eluted with ether-hexane (1:20, v/v)

Sources & evidence

ORD record
ord-5a2997ba5c8347609618bd24edfb5461
Source dataset
uspto-grants-1999_10
Patent number
US05965589

Reaction notes

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