Water → HCID 57479269, compound

At room temperature, NaOCH3 (335 mg, 6.19 mmol) was added to a solution of 1,3-dioxan-2-ylmethyltributylphosphoniumbromide (C. Spangler; R. McCoy, Synthetic communications, 18, 51, (1988)) (5.17 ml, 1 M in DMF, 5.71 mmol) and 4,5-dimethoxy-2-nitro-benzaldehyde (1.25 g, 4.76 mmol) in DMF (20 ml). After heating the mixture at 50° for overnight, the mixture was poured over water, and extracted with ether, washed with brine and dried over MgSO4. The solvent was evaporated and the residue was dissolved in THF (100 ml) and treated with 2 N HCl (50 ml). After stirring the mixture at room temperature for 2 h, the THF was evaporated, and the yellow solid was filtered, and suspended in ether/ethylacetate 4:1. The suspension stirred at room temperature for 1 h, filtered and washed with ether to afford (E)-3-(4,5-dimethoxy-2-nitro-phenyl)-propenal (624 mg, 55%) as a yellow solid, m.p. 103-105°. IR (KBr): 1689, 1605 cm-1. MS (EI): 237 (M).

1. temperatureAfter heating the mixture at 50° for overnight
2. extractionextracted with ether
3. washwashed with brine
4. dry with materialdried over MgSO4
5. customThe solvent was evaporated
6. dissolutionthe residue was dissolved in THF (100 ml)
7. additiontreated with 2 N HCl (50 ml)
8. customthe THF was evaporated
9. filtrationthe yellow solid was filtered
10. stirringThe suspension stirred at room temperature for 1 h
11. filtrationfiltered
12. washwashed with ether

ORD record

ord-9ce58923aa884971a77f4b0e573434cd

Source dataset

uspto-grants-2000_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06084120