Triethylamine → Methyl 3-phenyl-4-isoxazolecarboxylate

HRID 1897320Notes

Reaction equation

HRID 1897320 reaction equation
[OH:1]/[N:2]=[C:3](\Cl)/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:11][O:12][C:13](/[CH:15]=[CH:16]/OC(=O)C1C=CC([N+]([O-])=O)=CC=1)=[O:14].C(N(CC)CC)C>ClCCl>[CH3:11][O:12][C:13]([C:15]1[C:3]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[N:2][O:1][CH:16]=1)=[O:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5706359Alpha-chlorobenzaldoximeHCID 5706833[(E)-3-methoxy-3-oxoprop-1-enyl] 4-nitrobenzoate

Product 1

HCID 10750662Methyl 3-phenyl-4-isoxazolecarboxylateYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of (E)- and/or (Z)—N-hydroxy-benzenecarboximidoyl chloride (12.0 g, 77 mmol) and 4-nitro-benzoic-acid (E)-2-methoxycarbonyl-vinyl ester (9.7 g, 39 mmol) in dichloromethane (200 mL) was added triethylamine (20.9 mL, 150 mml) and the resulting solution stirred overnight at room temperature. The mixture was then diluted with dichloromethane (500 mL) and the organic extract removed and washed with water, dried over sodium sulfate and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 4:1) afforded the title product (3.1 g, 40%) which was obtained as a light yellow oil. MS: m/e=204.2 [M+H]+

Workup

  1. extractionthe organic extract
  2. customremoved
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 4:1)

Sources & evidence

ORD record
ord-56388e20774247ada5a7e161358ffff3
Source dataset
uspto-grants-2013_08
Patent number
US08518974B2

Reaction notes

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