Tetrahydrofuran → 4-Methoxy-2-(2-methyl-[1,3]-dioxolan-2-yl)benzoxazole-7-carboxylic acid
Reaction equation
Br[C:2]1[C:10]2[O:9][C:8]([C:11]3([CH3:16])[O:15][CH2:14][CH2:13][O:12]3)=[N:7][C:6]=2[C:5]([O:17][CH3:18])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[C]=[O:56].[O:57]1[CH2:61]CCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:18][O:17][C:5]1[C:6]2[N:7]=[C:8]([C:11]3([CH3:16])[O:15][CH2:14][CH2:13][O:12]3)[O:9][C:10]=2[C:2]([C:61]([OH:57])=[O:56])=[CH:3][CH:4]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
7-Bromo-4-methoxy-2-(2-methyl-[1,3]-dioxolan-2-yl)benzoxazole (480 mg), palladium acetate (34 mg), 1,3-bis(diphenylphosphino)propane (126 mg), triethylamine (0.21 ml), water (15 ml) and tetrahydrofuran (30 ml) were combined and heated to 90° C. in a Parr apparatus under 1035 kPa (150 psi) of carbon monoxide for 3 days. After cooling to room temperature, the tetrahydrofuran was evaporated in vacuo. The residue was partitioned between ethyl acetate (50 ml) and water (50 ml). The aqueous layer was extracted with ethyl acetate (50 ml). The combined organic extracts were dried over magnesium sulphate, evaporated in vacuo and purified by flash chromatography eluting with ethyl acetate to yield the title compound as a white solid (190 mg).
Workup
- customthe tetrahydrofuran was evaporated in vacuo
- customThe residue was partitioned between ethyl acetate (50 ml) and water (50 ml)
- extractionThe aqueous layer was extracted with ethyl acetate (50 ml)
- dry with materialThe combined organic extracts were dried over magnesium sulphate
- customevaporated in vacuo
- custompurified by flash chromatography
- washeluting with ethyl acetate
Sources & evidence
- ORD record
- ord-c26c330d25cb49308191857aa8d3dfd8
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06353010B1
Reaction notes
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