Methanol → 2-(Benzo[c][1,2,5]oxadiazol-5-yl)acetaldehyde

온도

25 °C

To a solution of 5-Allyl-2,1,3-benzoxadiazole (4.1 g, 26 mmol) in a solution of MeOH (30 mL), THF (50 mL), and water (20 mL) was added Osium Tetraoxide (6.0 mL 4% aq. solution, 0.77 mmol) and NMO (4.5 g, 38 mmol). The mixture was allowed to stir at 25° C. for 16 hours. TLC showed complete reaction. The reaction was diluted with water (200 mL) and extracted with EtOAc (200 mL×2). The extractions were combined, washed with brine, dried over sodium sulfate, and concentrated. The resulting product was redissolved in water and methanol (50 mL each), and cooled to 0° C. To that solution was added an aqueous solution of sodium periodate (7.2 g, 33 mmol). TLC showed complete reaction within 15 minutes. The reaction was diluted with water (100 mL) and extracted with EtOAc (100 mL×2). The extractions were combined, washed with brine, dried over sodium sulfate, and concentrated to obtain the product which was used in the next step without further purification.

1. customreaction
2. extractionextracted with EtOAc (200 mL×2)
3. extractionThe extractions
4. washwashed with brine
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated
7. dissolutionThe resulting product was redissolved in water
8. temperaturemethanol (50 mL each), and cooled to 0° C
9. customreaction within 15 minutes
10. extractionextracted with EtOAc (100 mL×2)
11. extractionThe extractions
12. washwashed with brine
13. dry with materialdried over sodium sulfate
14. concentrationconcentrated
15. customto obtain the product which
16. customwas used in the next step without further purification

ORD 기록

ord-e1d2bed06a8441af83f709079c9d5970

출처 데이터셋

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08999990B2