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

HRID 50583

反応式

HRID 50583 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒3 回

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-dd254f3cb7854e2ea9bea3f6e077f602
出典データセット
uspto-grants-2004_03
特許番号
US06713452B2

関連ノート

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