Tetrahydrofuran → HCID 19835535, compound

HRID 227355

Reaction equation

HRID 227355 reaction equation
CO[C:3]1[C:4]([N+:16]([O-:18])=[O:17])=[C:5]([CH:9]=[C:10](OC)[C:11]=1[O:12][CH3:13])[C:6](O)=O.C1C[O:22][CH2:21]C1>>[CH3:13][O:12][C:11]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:21][OH:22])=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1

Participants

3

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 971163,4,5-Trimethoxy-2-nitrobenzoic acid

Product 1

HCID 19835535HCID 19835535, compound

Procedure

To a stirred solution of the 3,4,5-Trimethoxy-2-nitrobenzoic acid (2 g, 7.77 mmol) and BH3 (1.0 M in THF, 13.2 ml) in THF (10 ml) was stirred and refluxed for 3 hours. After cooling, the reaction mixture was extracted with water and CH2Cl2. The combined organic layers were dried over MgSO4, and then evaporated to afford 4-methoxy-2-nitrobenzyl methanol. The crude 4-methoxy-2-nitrobenzyl methanol was dissolved in anhydrous CH2Cl2 (20 mL) and was subjected to pyridinium dichromate, PDC oxidation (5.84 g, 15.55 mmol)/molecular sieves (powder, 6 g) at room temperature for 16 h. The reaction mixture was filtrated by Celite and extracted with water and CH2Cl2. The organic layers were combined and evaporated. The residue was purified by flash chromatography (EtOAc:n-hexane=1:1) to afford compound A1 as a yellow solid, yield 69%. mp 73.8-75.1° C., 1H NMR (500 MHz, CDCl3) δ 3.97 (s, 3H), 3.99 (s, 6H), 7.21 (s, 1H), 9.86 (s, 1H).

Workup

  1. temperaturerefluxed for 3 hours
  2. temperatureAfter cooling
  3. extractionthe reaction mixture was extracted with water and CH2Cl2
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-4b32fdf2bb3a4bfc99e1d7c520aabd1c
Source dataset
uspto-grants-2009_07
Patent number
US07560491B2

Linked notes

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