Triethylene glycol di-p-tosylate → Triethylene Glycol

HRID 2221312ノート

反応式

HRID 2221312 の反応式
S([O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20]S(C1C=CC(C)=CC=1)(=O)=O)(C1C=CC(C)=CC=1)(=O)=O>C(OCC)(=O)C>[CH2:12]([OH:11])[CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][OH:20]

参加物

3

反応物 1

HCID 316652Triethylene glycol di-p-tosylate

生成物 1

HCID 8172Triethylene Glycol収率 89%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a 25 mL schlenk flask with Kontes valve and stirbar under argon 1 (1.67 mmol, 0.423 g) was added and the flask evacuated and backfilled with argon 3×. Anhydrous DMF (12.2 mL) was added via syringe and the solution stirred at rt. Next, anhydrous CsCO3 (3.52 mmol, 1.15 g) was added followed by triethylene glycol ditosylate (0.808 mmol, 0.371 g) and the mixture stirred at rt. The vessel was closed, stirred and heated to 70° C. for ca. 12 h. The reaction was allowed to cool to rt then diluted with ethyl acetate (10 mL), filtered and the solid washed with ethyl acetate (3×100 mL) and filtered. The organic extracts were combined and washed with saturated NH4Cl(aq) (25 mL) then washed with brine (3×25 mL) dried over Na2SO4, filtered and the solvent removed by rotovaporation to afford the crude product. Purification by silica plug (ethyl acetate) afforded a white solid (0.464 g; 89% yield). IR (cm−1) 2947, 2884, 1683, 1601, 1476, 1397, 1110; 1H NMR (400 MHz, CDCl3) δ 7.38 (s, 4H, ArH), 6.13 (s, 4H, ArCHO2), 4.18 (m, 4H, ArOCH2—), 4.02 (m, 16H, OCH2CH2O), 3.84 (m, 4H, ArOCH2CH2—), 3.78 (s, 4H, ArOCH2CH2OCH2CH2OCH2CH2OAr), 2.33 (s, 6H, ArCH3); {1H} 13C NMR (100 MHz, CDCl3) 154.5, 134.2, 130.8, 129.0, 99.1, 76.0, 70.9, 70.5, 65.5, 21.2.

後処理

  1. additionTo a 25 mL schlenk flask with Kontes valve and stirbar under argon 1 (1.67 mmol, 0.423 g) was added
  2. customthe flask evacuated
  3. additionAnhydrous DMF (12.2 mL) was added via syringe
  4. stirringthe mixture stirred at rt
  5. customThe vessel was closed
  6. stirringstirred
  7. temperatureheated to 70° C. for ca. 12 h
  8. temperatureto cool to rt
  9. filtrationfiltered
  10. washthe solid washed with ethyl acetate (3×100 mL)
  11. filtrationfiltered
  12. washwashed with saturated NH4Cl(aq) (25 mL)
  13. washthen washed with brine (3×25 mL)
  14. dry with materialdried over Na2SO4
  15. filtrationfiltered
  16. customthe solvent removed by rotovaporation

出典と根拠

ORDレコード
ord-1f92ee3e81e94a029751caa56446d060
出典データセット
uspto-grants-2008_05
特許番号
US07368564B2

反応ノート

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