Water → (3-Methoxyphenyl)(2-(2,4,6-trimethoxybenzylthio)phenyl)methanol

HRID 1158203노트

반응식

HRID 1158203 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH2:9][C:10]1[C:15]([O:16][CH3:17])=[CH:14][C:13]([O:18][CH3:19])=[CH:12][C:11]=1[O:20][CH3:21].[Li]CCCC.[CH3:27][O:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH:32]=[O:33].O>C1COCC1.CCCCCC.C(OCC)(=O)C>[CH3:27][O:28][C:29]1[CH:30]=[C:31]([CH:32]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8][CH2:9][C:10]2[C:15]([O:16][CH3:17])=[CH:14][C:13]([O:18][CH3:19])=[CH:12][C:11]=2[O:20][CH3:21])[OH:33])[CH:34]=[CH:35][CH:36]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 115693-MethoxybenzaldehydeHCID 66870845(2-Bromophenyl)(2,4,6-trimethoxybenzyl)sulfaneHCID 178418339Butyllithium

생성물 1

HCID 68643652(3-Methoxyphenyl)(2-(2,4,6-trimethoxybenzylthio)phenyl)methanol수율 70%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 21226206Ethyl acetate hexane용매

실험 절차

To a solution of 0.35 g (2-bromophenyl)(2,4,6-trimethoxybenzyl)sulfane (0.96 mmol) in dry THF was added slowly 1.2 eq n-BuLi. The reaction was stirred 25 minutes at −78° C. before 1.2 eq 3-methoxybenzaldehyde was added slowly. The reaction was warmed to ambient temperature and stirred for one additional hour before the addition of water. The mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. Flash silica chromatography (hexane:ethyl acetate 80:20) afforded 0.288 g product (0.68 mmol, 70% yield).

후처리

  1. additionwas added slowly
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e9e4de51aafc4a4f99f02489027f754c
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807713B2

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