Triphenylphosphine → HCID 59448133, compound

HRID 1920890Notes

Reaction equation

HRID 1920890 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].O[C:16]1[CH:20]=[C:19]([CH3:21])[O:18][N:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[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][O:14][C:16]1[CH:20]=[C:19]([CH3:21])[O:18][N:17]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 24781HymexazolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2776149(5-Methyl-3-phenyl-1,2-oxazol-4-yl)methanol

Product 1

HCID 59448133HCID 59448133, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (5-methyl-3-phenyl-isoxazol-4-yl)-methanol (378 mg, 2.0 mmol) in THF (7 mL) was added 3-hydroxy-5-methylisoxazole (200 mg, 2.0 mmol) and triphenylphosphine (629 mg, 2.0 mmol) at room temperature under an argon atmosphere. Then diethyl azodicarboxylate (˜40% in toluene, 1.1 mL, 2.5 mmol) was added and the reaction mixture was stirred for 3 h at room temperature. Concentration and purification by chromatography (silica, heptane:ethyl acetate=6:4 to 0:1) afforded the title compound (214 mg, 40%) as a colourless oil. MS: m/e=271.0 [M+H]+.

Workup

  1. concentrationConcentration and purification by chromatography (silica, heptane:ethyl acetate=6:4 to 0:1)

Sources & evidence

ORD record
ord-b0290e83cf3c4ae0816fcde711b8bba4
Source dataset
uspto-grants-2012_05
Patent number
US08173652B2

Reaction notes

Loading…