Alcohols 2- ethoxymethyl chloride

Thiazole acid chlorides react with diazomethane to give the diazoketone. The later reacts with alcoholic hydrogen chloride to give chloroacetylthiazole (Scheme 16). However, the Wolff rearrangement of the diazoketone is not consistently satisfactory (82). Heated with alcohol in the presence of copper oxide the 5-diazomethylketone (24) gives ethyl 5-thiazoleacetate (25) instead of the expected ethoxymethyl 5-thiazolyl ketone (Scheme 17) (83). 

The sodium or potassium alkoxide prepared from primary and secondary alcohols and sodium hydride or potassium hydride in THF reacts with 2-(trimethyl-silyi)ethoxymethyl chloride (SEMCl, bp 57-59 PC/1 kPa, HAZARD carcinogenic) to give the SEM ethers in good yield [Scheme 4.304]481 Alternatively, the alcohol can be alkylated with SEMC1 in the presence of f-PrjNEt in dichloro-methane at 4013 C [Scheme 4.305].257,525,555 Conversion of the SEMCl to the corresponding iodide in situ using tetrabutylammonium iodide accelerates the reaction ... 

Primary, secondary and tertiary alcohols can be protected in good yield as their 2-(trimethylsil-yl)ethoxymethyl ethers (abbreviated SEM ethers) by reaction with 2-(trimethylsilyl)ethoxymethyl chloride (SEM-Cl) in dichloromethane in the presence of Pr 2NEt. The resultant ethers are stable to the conditions used to remove THP and TMS ethers (3 1 1 THF HOAc H20). Deprotection takes place on treatment with TBAF in THF at 45 °C. 

ALCOHOLS Allyltrimethylsilane. (1 5-Cyclooctadiene)bis(methyldiphenylphos-phine)iridium hexafluorophosphate. Guaiacylmethyl chloride. Levulinic acid. )3-(Trimethylsilyl)ethoxymethyl chloride. 2-(Tiimethylsilyl)ethyl chloroformate. 

N-Benzyldimethylamine Benzyltriethyl ammonium chloride Benzyl trimethyl ammonium chloride Bis (2-ethylhexyl) maleate Bis (glycidoxypropyl) tetramethyidisiloxane 3-[Bis (2-hydroxyethyl) amino] propyltriethoxysilane N,N -Bis (2-hydroxypropyl)-2-methylpiperazine Bis-(N-methylbenzamide) ethoxymethyl silane Bisphenol A ethoxylate diacrylate Bis-(3-(triethoxysilyl) propyl) tetrasulfane Bis (trimethoxysilylpropyl) ethylene diamine Bis (trimethylsilyl) urea 1-Butoxyethoxy-2-propanol Butoxytriglycol t-Butyl alcohol n-Butyl chloroformate n-Butyldimethylchlorosilane Butyl lactate t-Butyl mercaptan Butyl myristate t-Butyl perbenzoate Butyl sulfide Calcium undecylenate C8-10 alcohols C14-15 alcohols... 

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