Aldoxime → 1-(3-Methyl-1,2-oxazol-5-yl)ethan-1-ol

To a stirring solution of 5.2 mL (84.9 mmol) of acetaldehyde oxime, 6.7 mL (85.5 mmol) of 3-butyn-2-ol, and 1.2 mL (8.6 mmol) of Et3N in 20 mL of CH2Cl2 at 0° C. was added 275 mL of NaOCl over a period of 2 h 45 min. The ice bath was removed and stirring was continued at r.t. for 18 h. Chloroform was added, and the layers were separated. The organic layer was extracted with CHCl3 (2×) and with the extract of a mixture of (80 mL CHCl3: 10 mL H2O: 10 mL MeOH) (2×). The combined extracts were dried over Na2SO4, filtered and concentrated. Purification by flash silica gel chromatography (2% MeOH/CHCl3) provided 2.2 g of 1-(3-methylisoxazol-5-yl)ethanol as an orange-yellow oil in 20% yield.

1. customThe ice bath was removed
2. additionChloroform was added
3. customthe layers were separated
4. extractionThe organic layer was extracted with CHCl3 (2×)
5. extractionwith the extract of a mixture of (80 mL CHCl3: 10 mL H2O: 10 mL MeOH) (2×)
6. dry with materialThe combined extracts were dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated
9. customPurification by flash silica gel chromatography (2% MeOH/CHCl3)

ORD record

ord-058286c0a8fa43de95442814099db85b

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07504420B2