p-Toluenesulfonic acid → HCID 19021020, 화합물

HRID 1109618노트

반응식

HRID 1109618 반응식
[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]

참가 물질

6

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 31214Ethyl orthoformateHCID 19021024HCID 19021024, 화합물

생성물 1

HCID 19021020HCID 19021020, 화합물

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5369fcbaf2724bceabd2f6364d3fa679
출처 데이터셋
uspto-grants-1994_06
특허 번호
US05321141

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