p-Toluenesulfonic acid → HCID 19021020、化合物

HRID 1109618ノート

反応式

HRID 1109618 の反応式
[Cl:1][C:2]1[S:6][N:5]([CH2:7][CH2:8]C=O)[C:4](=[O:11])[CH:3]=1.[CH:12]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])OCC.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>C(O)C>[CH2:20]([O:19][CH:12]([O:16][CH2:17][CH3:18])[CH2:8][CH2:7][N:5]1[C:4](=[O:11])[CH:3]=[C:2]([Cl:1])[S:6]1)[CH3:21]

参加物

6

反応物 4

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 31214Ethyl orthoformateHCID 19021024HCID 19021024、化合物

生成物 1

HCID 19021020HCID 19021020、化合物

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of compound 5 (2.5 g, 0.013 mole), triethyl orthoformate (3.87 g, 0.026 mole) in 20 ml ethanol and p-toluenesulfonic acid (35 mg) was refluxed for 18 hours. Upon cooling, the mixture was treated with 0.2 ml of triethylamine and extracted with diethyl ether. The extract was then washed successively with NaHCO3 solution, water and brine. After drying (MgSO4), the solvent was removed in vacuo. The residual brown oil was purified by column chromatography on silica gel, using diethyl ether/hexane (4/1) as eluant. The product was obtained as a light brown oil; 2.2 g; IR (neat) 1625 cm-1 ; NMR (CDCl3) δ6.3 (s, 1H); 4.6 (t, 1H); 3.85 (t, 2H); 3.4-3.8 (m, 4H); 2.0 (q, 2H); 1.2 (t, 6H).

後処理

  1. temperatureUpon cooling
  2. extractionextracted with diethyl ether
  3. washThe extract was then washed successively with NaHCO3 solution, water and brine
  4. dry with materialAfter drying (MgSO4)
  5. customthe solvent was removed in vacuo
  6. customThe residual brown oil was purified by column chromatography on silica gel
  7. customThe product was obtained as a light brown oil

出典と根拠

ORDレコード
ord-5369fcbaf2724bceabd2f6364d3fa679
出典データセット
uspto-grants-1994_06
特許番号
US05321141

反応ノート

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