In-situ generation of Et3SiBr from BiBr3 and Et3SiH and its use in preparation of dialkyl ethers

Tetrahedron Letters

Volumn 43, Issue 38, 2002, Pages 6709-6713

  Bajwa, Joginder S ^a   Jiang, Xinglong ^a   Slade, Joel ^a   Prasad, Kapa ^a   Repič, Oljan ^a   Blacklock, Thomas J ^a  

^a NOVARTIS INSTITUTES FOR BIOMEDICAL RESEARCH   (United States)

Author keywords

Bismuth bromide; Reductive etherification; Silyl ethers; Triethylsilane; Triethylsilyl bromide

Indexed keywords

ALCOHOL DERIVATIVE; ALKYL ETHER; BROMINE DERIVATIVE; CARBONYL DERIVATIVE; SILANE DERIVATIVE; SILICON DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; ETHERIFICATION; MOISTURE; REDUCTION;

EID: 0037119785     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01532-0     Document Type: Article

References (16)

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8. The following reaction conditions were tried: (a) NaH/THF/n-PrBr/rt/24 h; (b) NaH/THF/allyl bromide/rt/24 h; (c) NaH/THF/n-PrBr/18-crown-6/rt/24 h; and (d) NaH/DMF/allyl bromide/rt/24 h.
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10. 3-THF/reflux gave the following product:
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12. The structure of the product was found to be as follows:
13. 3 in wet acetonitrile: Bajwa J.S., Vivelo J., Slade J., Repic O., Blacklock T. Tetrahedron Lett. 41:2000;6021-6024.
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15. On large scale, the exotherm of the reaction was controlled by the rate of addition of propionaldehyde solution in acetonitrile to the reaction mixture and by external cooling.
16. 13C NMR δ 81.8, 71.9, 32.4, 29.9.