Oxazole → HCID 14786620, compound

Temperature

-78 °C

A round bottom flask was charged with oxazole (476 μL, 7.2 mmol) and THF (100 mL). The solution was cooled to −78° C. A solution of n-butyllithium (2.3M in hexanes, 3.5 mL, 8.05 mmol) was added dropwise. After stirring at −78° C. for 40 min, a solution of oxazole-4-carbaldehyde (773 mg, 7.96 mmol, in 8 mL THF) was added dropwise. The reaction was allowed to warm to room temperature. After 30 min, the reaction was quenched with sat NH4Cl and extracted with CH2Cl2 (3×). The organics were dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was chromatographed on a silica gel column (100% CH2Cl2 to 10% MeOH in CH2Cl2) and yielded bis(oxazol-4-yl)methanol (354 mg, 29%) as a light brown solid. 1H NMR 400 MHz (CDCl3) δ 7.93 (s, 2H), 7.73 (s, 2H), 5.87 (s, 1H), 3.52 (s, 1H). LCMS (ESI, m/z): 167 [M+H]+.

1. temperatureto warm to room temperature
2. waitAfter 30 min
3. customthe reaction was quenched with sat NH4Cl
4. extractionextracted with CH2Cl2 (3×)
5. dry with materialThe organics were dried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe residue was chromatographed on a silica gel column (100% CH2Cl2 to 10% MeOH in CH2Cl2)

ORD record

ord-d328855cbc5d4d93bc7868cf3fd71703

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133148B2