1-(Chloromethoxy)-2-methoxyethane → 2-[1-(Methoxyethoxymethoxy)ethyl]-3-methylthiothiophene
Reaction equation
[OH:1][CH:2]([C:4]1[S:5][CH:6]=[CH:7][C:8]=1[S:9][CH3:10])[CH3:3].[CH3:11][O:12][CH2:13][CH2:14][O:15][CH2:16]Cl.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[CH3:11][O:12][CH2:13][CH2:14][O:15][CH2:16][O:1][CH:2]([C:4]1[S:5][CH:6]=[CH:7][C:8]=1[S:9][CH3:10])[CH3:3]Participants
Procedure
To a stirred solution of 2-(1-hydroxyethyl)3-methylthiothiophene (13.5 g, 0.077 mol) in dry methylene chloride (100 ml) was added methoxyethoxymethyl chloride (11.5 g, 0.092 mol) followed by N,N-diisopropylethylamine (12.1 g, 0.092 mol) with cooling. The solution was stirred at room temperature for 18 hours. Some starting material remained upon work up at this point. The material was recycled as above using 1/2 the above quantities of methoxyethoxymethyl chloride and N,N-diisopropylethyl amine. After 5 hours at room temperature the reaction was completed. The solution was washed with water, dilute HCl, saturated NaHCO3 solution and again with water. Then it was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. Pure product was obtained as a yellow oil (17.6 g, 87%). TLC confirmed the purity and NMR and mass spectrometry (M/Z=262) supported the structure.
Workup
- temperaturewith cooling
- waitAfter 5 hours at room temperature the reaction was completed
- washThe solution was washed with water, dilute HCl, saturated NaHCO3 solution and again with water
- dry with materialThen it was dried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-f59b579c31c041e8baf034b25603ad51
- Source dataset
- uspto-grants-1990_05
- Patent number
- US04929637
Reaction notes
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