1-(Chloromethoxy)-2-methoxyethane → 3-[1-(Methoxyethoxymethoxy)propyl]-2-methylthiothiophene

HRID 1651641Notes

Reaction equation

HRID 1651641 reaction equation
[OH:1][CH:2]([C:5]1[CH:9]=[CH:8][S:7][C:6]=1[S:10][CH3:11])[CH2:3][CH3:4].[CH3:12][O:13][CH2:14][CH2:15][O:16][CH2:17]Cl.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[CH3:12][O:13][CH2:14][CH2:15][O:16][CH2:17][O:1][CH:2]([C:5]1[CH:9]=[CH:8][S:7][C:6]=1[S:10][CH3:11])[CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 81531DiisopropylethylamineHCID 14700382α-Ethyl-2-(methylthio)-3-thiophenemethanol

Product 1

HCID 147003833-[1-(Methoxyethoxymethoxy)propyl]-2-methylthiothiopheneYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-(1-hydroxypropyl)2-methylthiothiophene (17.7 g, 0.094 mol) in dry methylene chloride (100 ml) was added methoxyethoxymethyl chloride (20.6 g, 0.165 mol) followed by N,N,-diisopropylethylamine (21.3 g, 0.165 mol). The mixture was stirred at room temperature overnight. The mixture was washed with water, dried over anhydrous Na2SO4, filtered and concentrated in vacuo at room temperature to give 24.4 g of amber oil (94% yield). NMR confirmed the structure and mass spectral analysis confirmed the molecular weight at 276.09.

Workup

  1. washThe mixture was washed with water
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo at room temperature

Sources & evidence

ORD record
ord-8423d97c6b3a4903b61957a607ae8d36
Source dataset
uspto-grants-1990_05
Patent number
US04929637

Reaction notes

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