Diphenylacetylene → Methyl 4,5-diphenylisoxazole-3-carboxylate

HRID 1804499

Reaction equation

HRID 1804499 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:15]([CH:18](C(OC)=O)[C:19]([O:21][CH3:22])=[O:20])([O-])=[O:16]>C1(C)C=C(C)C=C(C)C=1>[C:1]1([C:7]2[C:18]([C:19]([O:21][CH3:22])=[O:20])=[N:15][O:16][C:8]=2[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 10390DiphenylacetyleneHCID 226085Dimethyl nitromalonate

Product 1

HCID 13524801Methyl 4,5-diphenylisoxazole-3-carboxylateYield 14.04%

Reagents, catalysts & solvents 1

HCID 7947MesityleneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 1,2-diphenylethyne (1.53 g, 8.6 mmol) and dimethyl 2-nitromalonate (1.05 mL, 7.83 mmol) in mesitylene (11 ml) was heated to 150° C. for 18 hr. The volatiles were removed in vacuo and the residue was chromatographed on a 5×12 cm silica gel column eluting with 0-10% EtOAc/hexanes. The essentially pure fractions containing product were concentrated to afford methyl 4,5-diphenylisoxazole-3-carboxylate (307 mg, 1.1 mmol, 14.04% yield) as a light yellow solid. HPLC retention time=1.85 minutes (YMC Combi 4.6×30 mm S-5 ODS column) eluting with 10-90% aqueous methanol+0.1 TFA a 2 minute gradient.

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residue was chromatographed on a 5×12 cm silica gel column
  3. washeluting with 0-10% EtOAc/hexanes
  4. additionThe essentially pure fractions containing product
  5. concentrationwere concentrated

Sources & evidence

ORD record
ord-981de8c8eb3a41cf8a30fa7305b3704c
Source dataset
uspto-grants-2013_01
Patent number
US08354398B2

Linked notes

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