Potassium Carbonate → 2-{2-Hydroxymethyl-4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenoxy)-2-methylpropionic acid ethyl ester

HRID 1181137Notes

Reaction equation

[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15]S(C1C=CC(C)=CC=1)(=O)=O.[CH2:26]([O:28][C:29](=[O:43])[C:30]([O:33][C:34]1[CH:39]=[CH:38][C:37](O)=[CH:36][C:35]=1[CH2:41][OH:42])([CH3:32])[CH3:31])[CH3:27].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH2:26]([O:28][C:29](=[O:43])[C:30]([O:33][C:34]1[CH:39]=[CH:38][C:37]([O:15][CH2:14][CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:6][C:2]=2[CH3:1])=[CH:36][C:35]=1[CH2:41][OH:42])([CH3:32])[CH3:31])[CH3:27]

Participants

Conditions

Temperature: 80 °C

Procedure

A 25 mL round bottomed flask under a nitrogen atmosphere was charged with toluene-4-sulfonic acid 2-(5-methyl-2-phenyloxazol-4-yl)ethyl ester (0.77 g, 2.17 mmol), 2-(4-hydroxy-2-hydroxymethylphenoxy)-2-methylpropionic acid ethyl ester (0.5 g, 1.97 mmol), and absolute ethanol (10 mL). Potassium carbonate (0.54 g, 3.94 mmol, 325 mesh) was added, and the reaction was heated to 80° C. for 12 h. The mixture was concentrated and the crude residue was diluted with EtOAc (75 mL). The organic layer was washed with brine (2×), dried (Na2SO4), and concentrated to an oil. The crude product was purified using radial chromatography (EtOAc:Hex 5:95 to 35:65) to give a colorless oil (0.17 g, 20%). MS (ES) m/e 452 (M+1).

Workup

concentrationThe mixture was concentrated
additionthe crude residue was diluted with EtOAc (75 mL)
washThe organic layer was washed with brine (2×)
dry with materialdried (Na2SO4)
concentrationconcentrated to an oil
customThe crude product was purified

Sources & evidence

ORD record: ord-a4701063c5f64912bee090711a6a22b2
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07282501B2

Reaction notes

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