Trityl chloride → 2-{2-[2-(2-{2-[2-(11-Tritylsulfanyl-undecyloxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-ethanol
反応式
[SH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][OH:31].[C:32]1([C:38](Cl)([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C1COCC1>[C:38]([S:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][OH:31])([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1参加物
実験手順
To a solution of 2-{2-[2-(2-{2-[2-(11-mercapto-undecyloxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-ethanol (3) (1.22 g, 2.6 mmol) prepared according to the method of Pale-Grosdemange et al.†, dissolved in 10 mL of THF was added triphenylmethyl chloride (1.46 g, 5.2 mmol). After stirring at room temperature for 48 hours, the reaction mixture was concentrated. The crude residue was purified by flash chromatography (gradient elution, EtOAc to 20:1 EtOAc/MeOH) to afford 910 mg (49%) of 4. 1H NMR (CDC13, 400 MHz) d 7.36 (d, J=X Hz, 6 H), 7.22 (t, J=X Hz, 6 H), 7.15 (t, J=X Hz, 3 H), 3.72-3.48 (br m, 24 H), 3.40 (t, J=X Hz, 2 H), 2.08 (t, J=X Hz, 2 H), 1.52 (m, 2 H), 1.4-0.9 (br, 16 H). ES-MS: m/z 733.4 (M+Na+). † Pale-Grosdemange, C.; Simon, E. S.; Prime, K. L.; Whitesides, G. M. J. Am. Chem. Soc, 1991, 113, 12-20.
後処理
- concentrationthe reaction mixture was concentrated
- customThe crude residue was purified by flash chromatography (gradient elution, EtOAc to 20:1 EtOAc/MeOH)
出典と根拠
- ORDレコード
- ord-10d6eded56d14c198b592f8e404d7e5a
- 出典データセット
- uspto-grants-2008_10
- 特許番号
- US07439056B2
反応ノート
読み込み中…