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

HRID 1987480

Reaction equation

HRID 1987480 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-89ab2d10ee214669a96c8ff3e20eae51
Source dataset
uspto-grants-2009_06
Patent number
US07550505B2

Linked notes

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