Ethanol → HCID 16665215, compound

HRID 132600Notes

Reaction equation

[OH:1][C:2]1[C:10]2[O:9][C:8]([C:11]([C:13]3[C:14]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[N:15][O:16][C:17]=3[CH3:18])=[O:12])=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:25](O)[CH3:26].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH2:25]([O:1][C:2]1[C:10]2[O:9][C:8]([C:11]([C:13]3[C:14]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[N:15][O:16][C:17]=3[CH3:18])=[O:12])=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)[CH3:26]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (7-hydroxy-2-benzofuranyl)(5-methyl-3-phenyl-4-isoxazolyl)methanone (example 4) (100 mg, 0.31 mmol) in THF (3.1 mL) was added ethanol (19 mg, 24 μL, 0.42 mmol) and triphenylphosphine (109 mg, 0.42 mmoL) at room temperature. The resulting mixture was then cooled to 0° C. and diethyl azodicarboxylate (73 mg, 65 μL, 0.42 mmol) added. The resulting mixture was maintained at 0° C. for 30 min and then allowed to warm up to room temperature overnight. The mixture was then adsorbed onto SiO2 and purification by chromatography (SiO2, heptane:ethyl acetate:=100:0 to 75:25) afforded the title compound (90 mg, 83%) as a white solid. MS m/e: 348.4 [M+H]+.

Workup

temperatureThe resulting mixture was maintained at 0° C. for 30 min
temperatureto warm up to room temperature overnight
customThe mixture was then adsorbed onto SiO2 and purification by chromatography (SiO2, heptane:ethyl acetate:=100:0 to 75:25)

Sources & evidence

ORD record: ord-0a6090c4503b42ebb0e5f89ff6a31587
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07388025B2

Reaction notes

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