2,6-Dimethylphenol → Methyl 3-{[(2,6-dimethylphenyl)oxy]methyl}-5-(1-methylethyl)-4-isoxazolecarboxylate

HRID 2423448Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:30][C:31]1[C:35]([C:36]([O:38][CH3:39])=[O:37])=[C:34]([CH:40]([CH3:42])[CH3:41])[O:33][N:32]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[O:9][CH2:30][C:31]1[C:35]([C:36]([O:38][CH3:39])=[O:37])=[C:34]([CH:40]([CH3:42])[CH3:41])[O:33][N:32]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 2,6-dimethylphenol (184 mg, 1.51 mmol), triphenylphosphine (396 mg, 1.51 mmol), and methyl 3-(hydroxymethyl)-5-(1-methylethyl)-4-isoxazolecarboxylate (300 mg, 1.51 mmol) in toluene (4 mL) was slowly added diisopropyl azodicarboxylate (0.272 mL, 1.51 mmol). The solution was heated in a microwave reactor at 90° C. for 10 minutes and then allowed to stand at ambient temperature overnight. The solution was concentrated and purified by chromatography (silica gel, 2.5% acetone in hexanes) to afford methyl 3-{[(2,6-dimethylphenyl)oxy]methyl}-5-(1-methylethyl)-4-isoxazolecarboxylate (329 mg, 72%). 1H-NMR (400 MHz, DMSO-d6) δ 7.02-6.90 (m, 3H), 5.00 (s, 2H), 3.74 (s, 3H), 3.72 (septet, J=7 Hz, 1H), 2.17 (s, 6H), 1.28 (d, J=7 Hz, 6H).

Workup

concentrationThe solution was concentrated
custompurified by chromatography (silica gel, 2.5% acetone in hexanes)

Sources & evidence

ORD record: ord-eace987fd45b40818fbfdbb3ae67a20a
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960552B2

Reaction notes

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