Trityl chloride → 2-{2-[2-(2-{2-[2-(11-Tritylsulfanyl-undecyloxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-ethanol

HRID 2222068노트

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HRID 2222068 반응식
[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

참가 물질

4

반응물 2

HCID 6456Trityl chlorideHCID 1621829229-Sulfanyl-3,6,9,12,15,18-hexaoxanonacosan-1-ol

생성물 1

HCID 222425972-{2-[2-(2-{2-[2-(11-Tritylsulfanyl-undecyloxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-ethanol수율 49.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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 (CDCl3, 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.

후처리

  1. concentrationthe reaction mixture was concentrated
  2. customThe crude residue was purified by flash chromatography (gradient elution, EtOAc to 20:1 EtOAc/MeOH)

출처 및 근거

ORD 기록
ord-c8957057b78c4a4a994a5082b70a6822
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07371563B2

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