Methanol → 2-Propyl-4-(((2-tetrahydropyranyl)oxy)methyl)oxazole-5-methanol

Temperature

0 °C

To a solution of 2-propyl-4-(((2-tetrahydropyranyl)oxy)methyl)oxazole-5-carboxylic acid, methyl ester (1.68 g, 5.94 mmol), from step 53a above, in 60 mL of methylene chloride cooled to -78° C. was added DIBAL (1.0M in hexane, 15 mmol). The reaction mixture was then stirred for 15 minutes at 0° C., and methanol (1.5 mL) was added carefully to quench the reaction. Saturated potassium sodium tartrate (50 mL) was added, and the mixtrue was stirred for 1 hour at room temperature. The layers were separated, and the aqueous layer was extracted with methylene chloride. The organic solutions were combined, dried over MgSO4 and concentrated. The residue was chromatographed on silica gel, eluting with 20% ethyl acetate in hexane to 3% methanol in ethyl acetate, to afford 1.27 g of the title compound as an oil. MS m/z: 256 (M+H)+. NMR (CDCl3) δ:4.72-4.51 (m, 5H), 3.85 (m, 1H), 3.55 (m, 1H), 2.97 (t, J=6 Hz, 1H), 2.71 (t, J=7.5 Hz, 2H), 1.90-1.50 (m, 8H), 0.99 (t, J=7.5 Hz, 3H).

1. customto quench
2. customthe reaction
3. stirringthe mixtrue was stirred for 1 hour at room temperature
4. customThe layers were separated
5. extractionthe aqueous layer was extracted with methylene chloride
6. dry with materialdried over MgSO4
7. concentrationconcentrated
8. customThe residue was chromatographed on silica gel
9. washeluting with 20% ethyl acetate in hexane to 3% methanol in ethyl acetate

ORD record

ord-e3df8dac9d5d4948acdd1c08b5e39b08

Source dataset

uspto-grants-1997_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05597832