(E)-2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]-4-(hexa-2,5-dienyl)thiazole

Base Information

Chemical Name:(E)-2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]-4-(hexa-2,5-dienyl)thiazole
CAS No.:292073-49-5
Molecular Formula:C₂₉H₃₇NOSSi
Molecular Weight:475.77
Hs Code.:

Synonyms:(E)-2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]-4-(hexa-2,5-dienyl)thiazole

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Chemical Property of (E)-2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]-4-(hexa-2,5-dienyl)thiazole

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Technology Process of (E)-2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]-4-(hexa-2,5-dienyl)thiazole

There total 22 articles about (E)-2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]-4-(hexa-2,5-dienyl)thiazole 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: 85.0%

: 7486-35-3
tri-n-butyl(vinyl)tin

: 292073-48-4
4-((2E)-4-bromobut-2-enyl)-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]thiazole

: 292073-49-5
(E)-2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]-4-(hexa-2,5-dienyl)thiazole

Guidance literature:: With dichloro bis(acetonitrile) palladium(II); In 1-methyl-pyrrolidin-2-one; at 20 ℃; for 0.666667h;
DOI:10.1016/S0040-4020(03)01020-2

Reference yield: 67.0%

: 1826-67-1
vinyl magnesium bromide

: 292073-48-4
4-((2E)-4-bromobut-2-enyl)-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]thiazole

: 292073-49-5
(E)-2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]-4-(hexa-2,5-dienyl)thiazole

: 2-[2-(tert-butyl-diphenyl-silanyloxy)-1,1-dimethyl-ethyl]-4-(2-vinyl-but-3-enyl)-thiazole

Guidance literature:: With copper(l) iodide; In tetrahydrofuran; at -78 ℃; for 0.5h;
DOI:10.1016/S0040-4020(03)01020-2

Reference yield:

: 14002-80-3
Methyl 2,2-dimethyl-3-hydroxypropionate

: 292073-49-5
(E)-2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]-4-(hexa-2,5-dienyl)thiazole

Guidance literature:: Multi-step reaction with 11 steps

1: imidazole / dimethylformamide / 14 h / 20 °C

2: DIBAL / diethyl ether; hexane / 0.5 h / -78 °C

3: Et₃N; pyridine*SO₃; DMSO / CH₂Cl₂ / 0.33 h / 20 °C

4: 16.8 g / Et₃N / toluene / 12 h / 20 °C

5: 62 percent / chemical manganese dioxide; pyridine / benzene / 12 h / Heating

6: 91 percent / DIBAL / diethyl ether; hexane / 0.5 h / -78 °C

7: Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

8: 344 mg / LiBr / acetone; CH₂Cl₂ / 1 h / 20 °C

9: 94 percent / Pd(CH₃CN)2Cl₂ / 1-methyl-pyrrolidin-2-one / 0.17 h / 20 °C

10: 95 percent / CBr₄; Ph₃P / CH₂Cl₂ / 0 - 20 °C

11: 85 percent / Pd(CH₃CN)2Cl₂ / 1-methyl-pyrrolidin-2-one / 0.67 h / 20 °C

With pyridine; 1H-imidazole; manganese(IV) oxide; dichloro bis(acetonitrile) palladium(II); carbon tetrabromide; sulfur trioxide pyridine complex; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium bromide; In 1-methyl-pyrrolidin-2-one; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; benzene; 3: Parikh-Doering oxidation / 11: Stille coupling;
DOI:10.1016/S0040-4020(03)01020-2