HCID 22261246, compound → HCID 22261247, compound

A solution of 2-(3-bromophenyl)-5-methyl-4-oxazoleacetic acid (39.1 g, 0.13 mol) in dry THF (175 mL) was treated dropwise with borane-THF complex (227 mL of a 1.0 M solution in THF, 1.3 mol) over 2 h (reaction temperature to 35° C.). After stirring 2 h at room temperature under N2, the reaction was quenched with slow addition of methanol (60 mL) and stirred overnight at room temperature. The reaction was diluted with 1 N NaOH (50 mL) and extracted with CH2Cl2 (2×200 mL). The organic layer was washed with H2O (3×100 mL), dried (MgSO4), and the solvent removed in vacuo to give 38.7 g of crude product that was recrystallized from toluene (200 mL, wash solid with cold hexanes) to give 26.9 g (72%) of 2-(3-bromophenyl)-5-methyl-4-oxazoleethanol as a white powder. Mp 92-93° C.; 1H NMR (300 MHz, d6-DMSO) δ7.99 (s, 1H), 7.88 (d, J=7.7 Hz, 1H), 7.64 (d, J=7.7 Hz, 1H), 7.44 (t, J=7.7 Hz, 1H), 4.61 (t, J=5.5 Hz, OH), 3.63 (q, J=5.5 Hz, 2H), 2.60 (t, J=6.6 Hz, 2H), 2.32 (s, 3H).

1. custom(reaction temperature to 35° C.)
2. customthe reaction was quenched with slow addition of methanol (60 mL)
3. stirringstirred overnight at room temperature
4. additionThe reaction was diluted with 1 N NaOH (50 mL)
5. extractionextracted with CH2Cl2 (2×200 mL)
6. washThe organic layer was washed with H2O (3×100 mL)
7. dry with materialdried (MgSO4)
8. customthe solvent removed in vacuo
9. customto give 38.7 g of crude product that
10. customwas recrystallized from toluene (200 mL, wash solid with cold hexanes)

ORD record

ord-a122f0f5f39d4548b243f5f3976f551b

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06610696B2