Réaction #9075

Équation de réaction

methyl-4-(5-phenyloxazol-2-yl)-benzoate

DIBAL-H

sodium potassium tartrate

→

2-(4-hydroxymethylphenyl)-5-phenyloxazole

Solvants

CH2Cl2

CH2Cl2

Conditions de réaction

Traitement

1. 1
   Températureto warm to room temperature
2. 2
   workup.STIRRINGThe bi-phasic mixture was stirred rapidly for 60 min
3. 3
   Autrethe layers separated
4. 4
   Extractionthe aqueous layer was extracted with CH2Cl2 (2×10 mL)
5. 5
   SéchageThe combined organic fractions were dried (Na2SO4)
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated in vacuo

Mode opératoire

To a solution of methyl-4-(5-phenyloxazol-2-yl)-benzoate (56 mg, 0.19 mmol) in CH2Cl2 (8 mL) at −78° C. was added DIBAL-H (1 mL of a 1.0 M solution in CH2Cl2, 1.0 mmol) and the solution stirred at −78° C. for 90 min. A saturated aqueous solution of sodium potassium tartrate (5 mL) was added to the reaction and the mixture allowed to warm to room temperature. The bi-phasic mixture was stirred rapidly for 60 min, the layers separated and the aqueous layer was extracted with CH2Cl2 (2×10 mL). The combined organic fractions were dried (Na2SO4), filtered and concentrated in vacuo to afford the desired alcohol, 2-(4-hydroxymethylphenyl)-5-phenyloxazole, as a pale yellow oil (46 mg, 96%). 1H NMR (CDCl3) δ 3.41 (t, 1H (OH), J=7.0 Hz), 4.77 (d, 2H, J=7.0 Hz), 7.33 (m, 1H), 7.45 (m, 5H), 7.72 (d, 2H, J=6.4 Hz), 8.08 (d, 2H, J=8.1 Hz).

Source