Of sodium trimethoxyborohydrid

High yields (76-81%) of alcohols are also obtained by adding solutions of acyl chlorides in anhydrous dioxane or diethyl carbitol to a suspension of sodium borohydride in dioxane and brief heating of the mixtures on the steam bath [751], by stirring solutions of acyl chlorides in ether for 2-4 hours at room temperature with aluminum oxide (activity I) impregnated with a 50% aqueous solution of sodium borohydride (Alox) (yields 80-90%) [1014], by refluxing acyl chlorides with ether solutions of sodium trimethoxyborohydride [99], or by treatment of acyl chlorides in dichloromethane solutions with tetrabutylammonium borohydride at —78° [771]. A 94% yield of neopentyl alcohol was achieved by the reaction of trimethylacetyl chloride with tert-butylmagnesium chloride [324]. 

Complex hydrides can be used for the selective reduction of the carbonyl group although some of them, especially lithium aluminum hydride, may reduce the a, -conjugated double bond as well. Crotonaldehyde was converted to crotyl alcohol by reduction with lithium aluminum hydride [55], magnesium aluminum hydride [577], lithium borohydride [750], sodium boro-hydride [751], sodium trimethoxyborohydride [99], diphenylstarmane [114] and 9-borabicyclo[3,3,l]nonane [764]. A dependable way to convert a, -un-saturated aldehydes to unsaturated alcohols is the Meerwein-Ponndorf reduction [765]. 

Chemical reduction of aromatic aldehydes to alcohols was accomplished with lithium aluminum hydride [5i], alane [770], lithium borohydride [750], sodium borohydride [757], sodium trimethoxyborohydride [99], tetrabutylam-monium borohydride [777], tetrabutylammonium cyanoborohydride [757], B-3-pinanyl-9-borabicyclo[3.3.1]nonane [709], tributylstannane [756], diphenylstan-nane [114], sodium dithionite [262], isopropyl alcohol [755], formaldehyde (crossed Cannizzaro reaction) [i7i] and others. 

In the boron series, an analog of the alkoxyaluminum hydrides, viz. sodium trimethoxyborohydride (sodium trimethoxyhydroborate), has been shown to give aldehydes from acid chlorides but only in poor yield.2 As an exception, other workers found that the same reducing agent at -80 °C afforded the aldehyde (8) in 85% yield from the corresponding acid chloride. ... 

The third name above certainly is more likely to create a visual picture of the structure than the currently used sodium trimethoxyborohydride, (40). 

Azines and their Hydro- and Benzo-derivatives Pyridines - Synthesis. Reaction of N - Cbz-5-amino-1-pentene (3) with mercury (II) acetate followed by reduction of the resulting mercuri acetate with sodium trimethoxyborohydride in the presence of methyl acrylate gives the ester (4). This was converted into the tetrahydropyridone (5) by hydrogenolysis followed by warming ... 

Sodium borohydride, hydroxylamine hydrochloride, dimethylamine borane, sodium citrate, hydrazine monohydrate, sodium formate, trimethylamine borane, sodium trimethoxyborohydride and formaldehyde have all become routine reducing agents for the generation of metal nanopartides. 

In contrast, the mercurial enones (89) (obtained by specific solvomercuration of the corresponding pendant terminal olefins) are isolated, and on treatment with sodium trimethoxyborohydride are reductively cyclized to (90). Alkynes... 

Reactions.—The use of NaBH, in polar aprotic solvents as a convenient and effective source of nucleophilic hydrogen for the reduction of alkyl halides (and tosylates) to alkanes has been reported in full this year. This reagent is selective and does not affect other functional groups such as ester or nitrile (contrast LiAlH4). Sodium trimethoxyborohydride is an alternative, especially for reduction in the presence of alkene functions this report also includes details of a one-pot sequence from alcohols via the iodides to alkanes (Scheme 46). ... 

The reduction of the thiazolium salt, thiamine, has been investigated with sodium borohydride, trimethoxyborohydride, and lithium... 

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