Triphenylphosphine → 5-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridine-2-carboxylic acid ethyl ester

HRID 1962948Notes

Reaction equation

HRID 1962948 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][OH:14].[CH2:15]([O:17][C:18]([C:20]1[CH:25]=[CH:24][C:23](O)=[CH:22][N:21]=1)=[O:19])[CH3:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.C1(C)C=CC=CC=1>[CH2:15]([O:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([O:14][CH2:13][C:3]2[C:4]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[N:5][O:6][C:2]=2[CH3:1])=[CH:22][N:21]=1)=[O:19])[CH3:16]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2776149(5-Methyl-3-phenyl-1,2-oxazol-4-yl)methanolHCID 231458205-Hydroxypyridine-2-carboxylic acid ethyl ester

Product 1

HCID 666443955-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridine-2-carboxylic acid ethyl esterYield 43.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (5-methyl-3-phenyl-4-isoxazolyl)methanol (570 mg, 3.01 mmol) and 5-hydroxy-pyridine-2-carboxylic acid ethyl ester (655 mg, 3.92 mmol) in THF (15 mL) under argon was added triphenylphosphine (1.03 g, 3.93 mmol). Diethyl azodicarboxylate (1.71 mL of a 40% solution in toluene, 682 mg, 3.92 mmol) was added dropwise. After 20 h the reaction mixture was concentrated in vacuo, water was added, and the reaction mixture extracted with ethyl acetate. The combined organic extracts were dried, filtered and concentrated then purified by chromatography (silica, 10 to 60% ethyl actetate in heptane) afforded the title compound (440 mg, 43%) as a pink oil. MS: m/e=339.3 [M+H]+.

Workup

  1. concentrationAfter 20 h the reaction mixture was concentrated in vacuo, water
  2. additionwas added
  3. extractionthe reaction mixture extracted with ethyl acetate
  4. customThe combined organic extracts were dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthen purified by chromatography (silica, 10 to 60% ethyl actetate in heptane)

Sources & evidence

ORD record
ord-96259b67cf9a4471998d875621af99fa
Source dataset
uspto-grants-2013_04
Patent number
US08415379B2

Reaction notes

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