Potassium Carbonate → Ethyl 2-[4-(hydroxymethyl)phenyl]-1,3-oxazole-4-carboxylate

HRID 1716856Notes

Reaction equation

Cl[C:2]1[O:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.[OH:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[OH:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[O:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=2)=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of ethyl 2-chloro-1,3-oxazole-4-carboxylate (0.59 g, 3.36 mmol) in dioxane was treated with 4-(hydroxymethyl)phenyl boronic acid (0.766 g, 5.04 mmol), K2CO3 (0.929 g, 6.72 mmol), t-Bu3PhBF4 (0.049 g, 0.168 mmol) heated to 80° C. then treated with Pd2(dba)3 (0.154 g 0.168 mmol) and stirred overnight at 90° C. The reaction mixture was diluted with EtOAc, washed with water, saturated sodium chloride, dried over MgSO4 and concentrated in in vacuo. The resultant residue was purified by flash chromatography (silica, EtOAc:hexanes 20→50%) to give the title product in 70% yield, identified by NMR and mass spectral analyses. LCMS (ESI+) 248 (MH+).

Workup

washwashed with water, saturated sodium chloride
dry with materialdried over MgSO4
concentrationconcentrated in in vacuo
customThe resultant residue was purified by flash chromatography (silica, EtOAc:hexanes 20→50%)

Sources & evidence

ORD record: ord-5480ed18099c49f081b718c2ece56031
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803825B2

Reaction notes

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