1-bromomethyl-2-ethynyl-2-tert-butyldimethylsilyloxymethyl-1-phenylselenylcyclopropane

Base Information

Chemical Name:1-bromomethyl-2-ethynyl-2-tert-butyldimethylsilyloxymethyl-1-phenylselenylcyclopropane
CAS No.:951793-24-1
Molecular Formula:C₁₉H₂₇BrOSeSi
Molecular Weight:458.372
Hs Code.:

Synonyms:1-bromomethyl-2-ethynyl-2-tert-butyldimethylsilyloxymethyl-1-phenylselenylcyclopropane

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Chemical Property of 1-bromomethyl-2-ethynyl-2-tert-butyldimethylsilyloxymethyl-1-phenylselenylcyclopropane

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Technology Process of 1-bromomethyl-2-ethynyl-2-tert-butyldimethylsilyloxymethyl-1-phenylselenylcyclopropane

There total 5 articles about 1-bromomethyl-2-ethynyl-2-tert-butyldimethylsilyloxymethyl-1-phenylselenylcyclopropane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 40.4%

: 951793-23-0
2-tert-butyldimethylsilyloxymethyl-2-ethynyl-1-methylenecyclopropane

: 1666-13-3
diphenyl diselenide

: 951793-24-1
1-bromomethyl-2-ethynyl-2-tert-butyldimethylsilyloxymethyl-1-phenylselenylcyclopropane

Guidance literature:: With N-Bromosuccinimide; In dichloromethane; at -20 - -10 ℃; for 0.416667h;
DOI:10.1016/j.tet.2007.06.109

Reference yield:

: 951793-19-4
ethyl 2-hydroxymethyl-1-methylenecyclopropane 2-carboxylate

: 951793-24-1
1-bromomethyl-2-ethynyl-2-tert-butyldimethylsilyloxymethyl-1-phenylselenylcyclopropane

Guidance literature:: Multi-step reaction with 6 steps

1: 83 percent / LiAlH₄ / tetrahydrofuran / 4 h / Heating

2: 82 percent / DMAP; pyridine / CH₂Cl₂ / 24 h / 20 °C

3: 83.5 percent / pyridinium chloroformate / CH₂Cl₂ / 34 h / 20 °C

4: 94.6 percent / Ph₃P / CH₂Cl₂ / 1.5 h / 0 - 20 °C

5: 89 percent / BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C

6: 40.4 percent / N-bromosuccinimide / CH₂Cl₂ / 0.42 h / -20 - -10 °C

With pyridine; dmap; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; pyridinium chloroformate; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; 4: Wittig reaction;
DOI:10.1016/j.tet.2007.06.109

Reference yield:

: 951793-20-7
2-tert-butyldimethylsilyloxymethyl-2-hydroxymethyl-1-methylenecyclopropane

: 951793-24-1
1-bromomethyl-2-ethynyl-2-tert-butyldimethylsilyloxymethyl-1-phenylselenylcyclopropane

Guidance literature:: Multi-step reaction with 4 steps

1: 83.5 percent / pyridinium chloroformate / CH₂Cl₂ / 34 h / 20 °C

2: 94.6 percent / Ph₃P / CH₂Cl₂ / 1.5 h / 0 - 20 °C

3: 89 percent / BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C

4: 40.4 percent / N-bromosuccinimide / CH₂Cl₂ / 0.42 h / -20 - -10 °C

With N-Bromosuccinimide; n-butyllithium; pyridinium chloroformate; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; 2: Wittig reaction;
DOI:10.1016/j.tet.2007.06.109