Tetrahydrofuran → HCID 86619844, Verbindung

HRID 227357

Reaktionsgleichung

Reaktionsgleichung von HRID 227357
[CH3:1][O:2][C:3]1[C:4]([N+:16]([O-:18])=[O:17])=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6](O)=O.C1C[O:22][CH2:21]C1>>[CH3:1][O:2][C:3]1[C:4]([N+:16]([O-:18])=[O:17])=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[CH2:6][CH2:21][OH:22]

Komponenten

3

Edukt 2

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

Produkt 1

HCID 86619844HCID 86619844, Verbindung

Versuchsvorschrift

To a stirred solution of the 3,4,5-Trimethoxy-2-nitrobenzoic acid (5 g, 19.40 mmol) in THF (30 ml) was added by BH3 (1.0 M in THF, 29.1 ml) under nitrogen. The mixture was stirred and refluxed for 2 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 3,4,5-Trimethoxy-2-nitrobenzyl methanol. The crude 3,4,5-trimethoxy-2-nitrobenzyl methanol was dissolved in anhydrous CH2Cl2 (20 mL) and was subjected to PBr3 (2.40 ml, 25.22 mmol) in an ice bath. After 2 h, the mixture was extracted with water and CH2Cl2. The organic layers were combined and evaporated. The residue was purified by flash chromatography (EtOAc:n-hexane=1:2) to afford B1 as a pale yellow oil, yield 68%. 1H NMR (500 MHz, CDCl3) δ 3.90 (s, 3H), 3.92 (s, 3H), 3.98 (s, 3H), 4.44 (s, 2H), 6.72 (s, 1H).

Aufarbeitung

  1. temperaturerefluxed for 2 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

Quellen und Nachweise

ORD-Eintrag
ord-84203644bda849a8937f0deeb335d584
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560491B2

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