Diethylene Glycol Monomethyl Ether → Ethyl 2,5,8,11,14,17,20,23-octaoxanonacosan-29-oate

HRID 24991

반응식

HRID 24991 반응식
[H-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][O:7]CCO.[CH2:11]([O:13][C:14](=[O:42])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37]S(C)(=O)=O)[CH3:12]>C1(C)C=CC=CC=1>[CH2:11]([O:13][C:14](=[O:42])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37][O:7][CH2:6][CH2:5][O:4][CH3:3])[CH3:12]

참가 물질

5

반응물 3

HCID 8134Diethylene Glycol Monomethyl EtherHCID 24758Sodium hydrideHCID 865870276-{2-[2-(2-{2-[2-(2-Methylsulfonylethoxy) ethoxy]ethoxy}-ethoxy)-ethoxy]-ethoxy}-hexanoic acid ethyl ester

생성물 1

HCID 71366717Ethyl 2,5,8,11,14,17,20,23-octaoxanonacosan-29-oate수율 62.6%

시약·촉매·용매 1

HCID 1140Toluene용매3회

반응 조건

온도
0 °C

실험 절차

NaH (88 mg of a 60% dispersion in oil, 2.2 mmol) was suspended in anhydrous toluene (3 ml) under N2 and chilled to 0° C. Non-polydispersed diethylene glycol monomethyl ether (0.26 ml, 0.26 g, 2.2 mmol) that had been dried via azeotropic distillation with toluene was added. The reaction mixture was allowed to warm to room temperature and stirred for four hours, during which time the cloudy grey suspension became clear and yellow and then turned brown. Mesylate 20 (0.50 g, 1.0 mmol) in 2.5 ml dry toluene was added. After stirring at room temperature over night, the reaction was quenched by the addition of 2 ml of methanol and the resultant solution was filtered through silica gel. The filtrate was concentrated in vacuo and the FAB MS: m/e 499 (M+H), 521 (M+Na). Additional purification by preparatory chromatography (silica gel, 19/3 chloroform/methanol) provided the non-polydispersed product as a clear yellow oil (0.302 g 57%). FAB MS: m/e 527 (M+H), 549 (M+Na).

후처리

  1. additionwas added
  2. temperatureto warm to room temperature
  3. stirringAfter stirring at room temperature over night
  4. customthe reaction was quenched by the addition of 2 ml of methanol
  5. filtrationthe resultant solution was filtered through silica gel
  6. concentrationThe filtrate was concentrated in vacuo
  7. customAdditional purification by preparatory chromatography (silica gel, 19/3 chloroform/methanol)

출처 및 근거

ORD 기록
ord-ae90c7b9f46d45c5938d1df1232066fd
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858580B2

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