Tetrahydrofuran → HCID 19835535, 화합물

HRID 227355

반응식

HRID 227355 반응식
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

참가 물질

3

반응물 2

HCID 8028Tetrahydrofuran2회HCID 971163,4,5-Trimethoxy-2-nitrobenzoic acid

생성물 1

HCID 19835535HCID 19835535, 화합물

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4b32fdf2bb3a4bfc99e1d7c520aabd1c
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560491B2

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