Tetrahydrofuran → Methyl 2-(p-methoxyphenyl)-1-methylthioethyl sulfoxide

HRID 1657877Notes

Reaction equation

HRID 1657877 reaction equation
[CH3:1][S:2][CH2:3][S:4]([CH3:6])=[O:5].O1CCCC1.[H-].[Na+].[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Br)=[CH:18][CH:17]=1>O.C(Cl)Cl>[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][CH:3]([S:4]([CH3:6])=[O:5])[S:2][CH3:1])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 99129Methyl (methylsulfinyl)methyl sulfideHCID 1650214-Methoxybenzyl bromide

Product 1

HCID 12219897Methyl 2-(p-methoxyphenyl)-1-methylthioethyl sulfoxideYield 79.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1.175 g of methyl methylthiomethyl sulfoxide was dissolved in 5 ml. of tetrahydrofuran, and under cooling with ice, 0.965 g (one equivalent) of sodium hydride was added. The mixture was then stirred for 1 hour. 1.93 g of p-methoxybenzyl bromide (1 equivalent) was added, and the mixture was stirred for 22 hours at room temperature, followed by addition of 40 ml. of methylene chloride and 2 ml. of water. The reaction mixture was dried with sodium sulfate anhydride, and concentrated at reduced pressure. The residue was subjected to column chromatography (silica gel, methylene chloride) to give 1.163 g of methyl 2-(p-methoxyphenyl)-1-methylthioethyl sulfoxide in a conversion yield of 79.1%.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for 22 hours at room temperature
  3. additionfollowed by addition of 40 ml
  4. dry with materialThe reaction mixture was dried with sodium sulfate anhydride
  5. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-2ae4a1a99a2f462c9c8e0772ab220e46
Source dataset
uspto-grants-1976_06
Patent number
US03962281

Reaction notes

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