1,10-Decanediol → HCID 86665351, 화합물

HRID 1471358노트

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HRID 1471358 반응식
CC1C=CC(S(O[C@@H:12]2[CH2:25][C:24]3[C@@:15]([CH3:38])([C@@H:16]4[C@@H:21]([CH2:22][CH:23]=3)[C@@H:20]3[CH2:26][CH2:27][C@H:28]([C@@H:29]([CH2:31][CH2:32][CH2:33][CH:34]([CH3:36])[CH3:35])[CH3:30])[C@@:19]3([CH3:37])[CH2:18][CH2:17]4)[CH2:14][CH2:13]2)(=O)=O)=CC=1.[CH2:39]([OH:50])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][OH:49]>O1CCOCC1>[CH3:36][CH:34]([CH2:33][CH2:32][CH2:31][C@H:29]([C@@H:28]1[C@:19]2([CH3:37])[C@H:20]([C@H:21]3[C@H:16]([CH2:17][CH2:18]2)[C@:15]2([CH3:38])[C:24]([CH2:25][C@@H:12]([O:50][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][OH:49])[CH2:13][CH2:14]2)=[CH:23][CH2:22]3)[CH2:26][CH2:27]1)[CH3:30])[CH3:35]

참가 물질

4

반응물 2

HCID 371531,10-DecanediolHCID 10907651Cholesteryl tosylate

생성물 1

HCID 86665351HCID 86665351, 화합물수율 82%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

In a 500 mL round-bottomed flask was cholesteryl tosylate (10.0 g, 18.5 mmol) and 1,10-Decanediol (48.3 g, 277 mmol) suspended in Dioxane (200 ml) to give a white suspension. The flask was fitted with a temperature sensor and reflux condenser. The mixture was heated to reflux and allowed to stir at reflux overnight. The reaction mixture was cooled to room temperature and the solids were filtered off. The solution was concentrated in vacuo. The mixture was re-dissolved in methanol (250 mL) and water (ca. 40 mL) was added to precipitate out the crude product. The precipitate was filtered and dried in vacuo. The residue was further purified via column chromatography on a 100 g Biotage SNAP column eluting over 2 L of a 0-25% EtOAc in Hexanes gradient. Pure fractions were combined and concentrated to give 7.85 g (82%) of a white solid. 1H NMR (300 mHz, CDCl3) δ0.69 (3H, s); 0.85-1.66 (50H, m); 1.75-2.09 (5H, m); 2.14-2.29 (1H, m); 2.32-2.43 (1H, m); 3.14 (1H, tt, J=11.2, 4.4 Hz); 3.46 (2H, dt, J=6.9, 0.4 Hz); 3.65 (2H, t, J=6.6 Hz); 5.36 (1H, d, J=5.3 Hz).

후처리

  1. customIn a 500 mL round-bottomed flask was
  2. customto give a white suspension
  3. customThe flask was fitted with a temperature sensor
  4. temperaturereflux condenser
  5. temperatureThe mixture was heated
  6. temperatureto reflux
  7. temperatureat reflux overnight
  8. filtrationthe solids were filtered off
  9. concentrationThe solution was concentrated in vacuo
  10. dissolutionThe mixture was re-dissolved in methanol (250 mL)
  11. additionwater (ca. 40 mL) was added
  12. customto precipitate out the crude product
  13. filtrationThe precipitate was filtered
  14. customdried in vacuo
  15. customThe residue was further purified via column chromatography on a 100 g Biotage SNAP column
  16. washeluting over 2 L of a 0-25% EtOAc in Hexanes gradient
  17. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3eef348817644c7cb80f15978e65dd47
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012225B2

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