2-{[4-(tert-butyldimethylsilyloxymethyl)pent-4-en-2-ynylamino]methyl}-6-(trimethylsilyl)phenol

Base Information

Chemical Name:2-{[4-(tert-butyldimethylsilyloxymethyl)pent-4-en-2-ynylamino]methyl}-6-(trimethylsilyl)phenol
CAS No.:866041-66-9
Molecular Formula:C₂₂H₃₇NO₂Si₂
Molecular Weight:403.712
Hs Code.:

Synonyms:2-{[4-(tert-butyldimethylsilyloxymethyl)pent-4-en-2-ynylamino]methyl}-6-(trimethylsilyl)phenol

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Chemical Property of 2-{[4-(tert-butyldimethylsilyloxymethyl)pent-4-en-2-ynylamino]methyl}-6-(trimethylsilyl)phenol

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Technology Process of 2-{[4-(tert-butyldimethylsilyloxymethyl)pent-4-en-2-ynylamino]methyl}-6-(trimethylsilyl)phenol

There total 5 articles about 2-{[4-(tert-butyldimethylsilyloxymethyl)pent-4-en-2-ynylamino]methyl}-6-(trimethylsilyl)phenol 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: 80.0%

: 866041-35-2
2-[(prop-2-ynylamino)methyl]-6-(trimethylsilyl)phenol

: 147455-22-9
1-(tert-butyldimethylsilyloxy)-2-iodoprop-2-ene

: 866041-66-9
2-{[4-(tert-butyldimethylsilyloxymethyl)pent-4-en-2-ynylamino]methyl}-6-(trimethylsilyl)phenol

Guidance literature:: With piperidine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1021/ol051372l

Reference yield:

: 824-91-9
O-methoxymethylphenol

: 866041-66-9
2-{[4-(tert-butyldimethylsilyloxymethyl)pent-4-en-2-ynylamino]methyl}-6-(trimethylsilyl)phenol

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 2 h / 0 °C

1.2: tetrahydrofuran; hexane / 0 - 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 2 h / 0 °C

2.2: 87 percent / tetrahydrofuran; hexane / -78 - 20 °C

3.1: 97 percent / NaI; HCl / acetone; H₂O / 0.75 h / 55 °C

4.1: molecular sieves 3 Angstroem / methanol / 0.5 h / 20 °C

4.2: 83 percent / NaBH₄ / methanol / 1 h / 0 °C

5.1: 80 percent / CuI; piperidine / (Ph₃P)2PdCl₂ / tetrahydrofuran / 1 h / 20 °C

With piperidine; hydrogenchloride; copper(l) iodide; n-butyllithium; 3 A molecular sieve; sodium iodide; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; hexane; water; acetone; 5.1: Sonogashira cross-coupling;
DOI:10.1021/ol051372l

Reference yield:

: 444095-29-8
2-hydroxy-3-(trimethylsilyl)benzaldehyde

: 866041-66-9
2-{[4-(tert-butyldimethylsilyloxymethyl)pent-4-en-2-ynylamino]methyl}-6-(trimethylsilyl)phenol

Guidance literature:: Multi-step reaction with 2 steps

1.1: molecular sieves 3 Angstroem / methanol / 0.5 h / 20 °C

1.2: 83 percent / NaBH₄ / methanol / 1 h / 0 °C

2.1: 80 percent / CuI; piperidine / (Ph₃P)2PdCl₂ / tetrahydrofuran / 1 h / 20 °C

With piperidine; copper(l) iodide; 3 A molecular sieve; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; 2.1: Sonogashira cross-coupling;
DOI:10.1021/ol051372l