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

HRID 1158203Notes

Reaction equation

HRID 1158203 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-e9e4de51aafc4a4f99f02489027f754c
Source dataset
uspto-grants-2010_10
Patent number
US07807713B2

Reaction notes

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