F butoxymethyl

The reagent forms the expected adducts with aldehydes and ketones in high yield. It can be used for preparation of f-butoxymethyl ketones from acid chlorides (equation I). In combination with CuBr, it undergoes conjugate addition to a,(3-enones (equation II). 

Proticlion of hydroxyl groups. f-Butoxymethyl ethers of alcohols can be obtained by rcaclion with <-butyl chloromethyl ether and triethylamine in THF at room tempcralure. The acetals are obtained in 55-80% yield. Yields are poor in the case of phenols. Deprotection is accomplished with TFA at room temperature. The acetals are stable to hot acetic acid therefore selective deprotection of other acid-sensitivc groups is possible. ... 

Methoxymethyl, 30 Methylthiomethyl, 38 (Phenyldimethylsilyl) methoxymethyl, 41 Benzyloxymethyl, 41 p-Methoxybenzyloxymethyl, 43 [(3,4-Dimethoxybenzyl)oxy] methyl, 43 p-Nitrobenzyloxymethyl, 44 o-Nitrobenzyloxymethyl, 44 [(i ) -1- (2-Nitrophenyl) ethoxy] methyl, 45 (4-Methoxyphenoxy)methyl, 45 Guaiacolmethyl, 46 [(p-Phenylphenyl)oxy]methyl, 47 f-Butoxymethyl, 47 4-Pentenyloxymethyl, 47 Siloxymethyl, 48 2-Methoxyethoxymethyl, 49 2-Cyanoethoxymethyl, 53 Bis(2-chloroethoxy)methyl, 53 2,2,2-Trichloroethoxymethyl, 53 2- (Trimethylsilyl) ethoxymethyl, 54 Menthoxymethyl, 58 0-Bis(2-acetoxyethoxy)methyl, 59 Tetrahydropyranyl, 59... 

CF3COOH, H20,20°C, 48 h, 85-90% yield. The f-butoxymethyl ether is stable to hot glacial acetic acid aqueous acetic acid, 20°C and anhydrous trifluoroacetic acid. 

W-Hydroxymethyl, 884 W-Methoxymethyl, 885 W-Diethoxymethyl, 885 W-(2-Chloroethoxy)methyl, 885 N- [2- (Trimethylsilyl) ethoxy]methyl, 885 W-f-Butoxymethyl, 886 W-f-Butyldimethylsiloxymethyl, 886 W-Pivaloyloxymethyl, 886 W-Benzyloxymethyl, 886 W-Dimethylaminomethyl, 887 W-2-Tetrahydropyranyl, 887... 

The dihalocyclopropane route is the method of choice for the synthesis of benzocyclopropenes and linearly fused cyclopropanaphthalenes, but is unsuccessful for angular cyclopropa[u]naph-thalene. Treatment of l,l-dichloro-la,2,3,7b-tetrahydro-l/f-cyclopropa[a]naphthalene(5) with potassium /ert-butoxide gave a mixture of 1-chloromethylnaphthalene, 1-terr-butoxymethyl-naphthalene and 2-terf-butoxy-l-chloromethylene-l,2,3,4-tetrahydronaphthalene, but none of the expected cyclopropa[n]naphthalene. The failure of the reaction has been attributed to difficulties in the aromatization. Isomerization of the initially produced cyclopropenyl double bond into the cyclohexane ring would require disruption of the aromatic character of the adjacent benzene nngT t-r>> 62 Similarly, attempted aromatization of l-chloro-l,2,3,7b-tetra-hydro-l//-cyclopropa[a]naphthalene (6) with 2,3-dichloro-5,6-dicyanobenzoquinone or via N-bromosuccinimide bromination followed by reaction with base afforded 4,5-benzotropone instead of cyclopropa[fl]naphthalenc. ... 

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