Tetrahydrofuran → HCID 86619844、化合物

HRID 227357

反応式

HRID 227357 の反応式
[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]

参加物

3

反応物 2

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

生成物 1

HCID 86619844HCID 86619844、化合物

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-84203644bda849a8937f0deeb335d584
出典データセット
uspto-grants-2009_07
特許番号
US07560491B2

関連ノート

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