CID 406 → Methyl [3-[2-(4,5-diphenyl-2-oxazolyl)ethenyl]phenoxy]acetate

HRID 257626Notes

Reaction equation

HRID 257626 reaction equation
[Na].[C:2]1([C:8]2[N:9]=[C:10]([CH2:19]P(=O)(OC)OC)[O:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:26]([C:28]1[CH:29]=[C:30]([CH:37]=[CH:38][CH:39]=1)[O:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])=O.P(=O)([O-])[O-]>CO>[C:2]1([C:8]2[N:9]=[C:10]([CH:19]=[CH:26][C:28]3[CH:29]=[C:30]([CH:37]=[CH:38][CH:39]=3)[O:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])[O:11][C:12]=2[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 406CID 406HCID 1494380Methyl 2-(3-formylphenoxy)acetateHCID 5360545SodiumHCID 54445617Dimethyl [(4,5-diphenyl-2-oxazolyl)methyl]phosphonate

Product 1

HCID 53907733Methyl [3-[2-(4,5-diphenyl-2-oxazolyl)ethenyl]phenoxy]acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium metal (260 mg, 11 mg atom) was dissolved in methanol (50 mL) and dimethyl [(4,5-diphenyl-2-oxazolyl)methyl]phosphonate (3.89 g, 11 mmol) added followed by methyl (3-formylphenoxy)acetate (2 g, 10 mmol). The mixture was stirred at room temperature for 20 minutes before being concentrated and diluted with 2N HCl solution. The mixture was extracted with CH2Cl2, the organic phase dried over sodium sulfate and the solvent evaported to leave a yellow oil. This was combined with the crude material from a reaction performed on 2 g of the phosphonate and 985 mg of aldehyde and chromatographed on a column of silica gel. Elution with a mixture of hexanes and diethyl ether (3:2) furnished methyl [3-[2-(4,5-diphenyl-2-oxazolyl)ethenyl]phenoxy]acetate as the diethyl ether solvate (2.92 g, 46%) after recrystallization from diethyl ether, m.p. 79°-82° C.

Workup

  1. concentrationbefore being concentrated
  2. additiondiluted with 2N HCl solution
  3. extractionThe mixture was extracted with CH2Cl2
  4. dry with materialthe organic phase dried over sodium sulfate
  5. customto leave a yellow oil
  6. customchromatographed on a column of silica gel
  7. washElution
  8. additionwith a mixture of hexanes and diethyl ether (3:2)

Sources & evidence

ORD record
ord-b6b259a1f7cc441f9591b6800a523a2e
Source dataset
uspto-grants-1993_11
Patent number
US05262540

Reaction notes

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