Potassium Hydroxide → 1,2,3-Trimethoxy-5-((4-methoxybenzyl)sulfanyl)benzene

HRID 583937Notes

Reaction equation

HRID 583937 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([SH:13])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].Cl[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1.[OH-].[K+].[NH4+].[Cl-]>CN(C=O)C>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([S:13][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 699934-Methyloxybenzyl chlorideHCID 151982403,4,5-Trimethoxybenzenethiol

Product 1

HCID 99016371,2,3-Trimethoxy-5-((4-methoxybenzyl)sulfanyl)benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A room temperature solution of Example 85A (194 mg, 0.97 mmol), 1-(chloromethyl)-4-methoxybenzene (162 mg, 1.03 mmol), and KOH (70 mg, 1.25 mmol) in DMF (5 mL) was stirred for 2 hours, treated with saturated NH4Cl, and extracted with ethyl acetate. The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 25% ethyl acetate/hexanes to provide the desired product.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was purified by flash column chromatography on silica gel with 25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-ac7b074d5c2f439b929a8381ad13f429
Source dataset
uspto-grants-2005_08
Patent number
US06924304B2

Reaction notes

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