Triphenylphosphine → methyl 3-[4-[[4-[(2Z)-2-methoxyimino-2-phenylethoxy]phenyl]methoxy]phenyl]-3-(1,2-oxazol-3-yl)propanoate

Temperature

0 °C

To a 50 mL RB flask fitted with magnetic stirrer was charged dry THF (5.0 mL) and methyl 3-(4-hydroxyphenyl)-3-(1,2-oxazol-3-yl)propanoate (0.18 g, 0.74 mmol). To the above mixture (4-{[(2Z)-2-(methoxyimino)-2-phenylethyl]oxy}phenyl)methanol (0.2 g, 0.74 mmol) was added and the resulting mixture stirred at 0° C. for 5 min. Triphenyl phosphine (0.25 g, 0.96 mmol) was added to the mixture and stirred at 0° C. for 15 min followed by the addition of diisopropylazadicarboxylate (0.19 g, 0.96 mmol). After stirring the resulting mixture at RT for 10 h, the RM was evaporated to remove the THF. The residue was diluted with water (15 mL) and extracted with ethyl acetate (15 mL×2). The organic layer was washed with saturated brine solution (15 mL) and dried over anhydrous Na2SO4. Concentration of the solvent and purification of the resulting residue by column chromatography on silica gel (100/200 mesh), using petroleum ether (60-80) and ethyl acetate (ratio) as eluant, gave the product (0.1 g, yield: 27.47%): MS (ESI, 120 eV): m/z=501.1 (M+H)+; 1H NMR (300 MHz, CDCl3): δ 8.20 (d, 1H), 7.57-7.60 (t, 2H), 7.22-7.28 (m, 5H), 7.07-7.10 (d, 2H), 6.81-6.85 (m, 4H), 5.99-6.00 (d, 1H), 5.12 (s, 2H), 4.85 (s, 2H), 4.47-4.52 (t, 1H), 3.98 (s, 3H), 3.56 (s, 3H), 3.18-3.26 (q, 1H), 2.82-2.90 (q, 1H).

1. customTo a 50 mL RB flask fitted with magnetic stirrer
2. stirringstirred at 0° C. for 15 min
3. additionfollowed by the addition of diisopropylazadicarboxylate (0.19 g, 0.96 mmol)
4. stirringAfter stirring the resulting mixture at RT for 10 h
5. customthe RM was evaporated
6. customto remove the THF
7. additionThe residue was diluted with water (15 mL)
8. extractionextracted with ethyl acetate (15 mL×2)
9. washThe organic layer was washed with saturated brine solution (15 mL)
10. dry with materialdried over anhydrous Na2SO4
11. customConcentration of the solvent and purification of the resulting residue by column chromatography on silica gel (100/200 mesh)

ORD record

ord-49581cfa88f442b79ea17e6ad1f222b2

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09278915B2