2-<2-(tert-Butyldimethylsiloxy)-4-methylphenyl>-2-cyclopropylideneethanol

Base Information

Chemical Name:2-<2-(tert-Butyldimethylsiloxy)-4-methylphenyl>-2-cyclopropylideneethanol
CAS No.:154699-03-3
Molecular Formula:C₁₈H₂₈O₂Si
Molecular Weight:304.505
Hs Code.:

Synonyms:2-<2-(tert-Butyldimethylsiloxy)-4-methylphenyl>-2-cyclopropylideneethanol

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Chemical Property of 2-<2-(tert-Butyldimethylsiloxy)-4-methylphenyl>-2-cyclopropylideneethanol

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Technology Process of 2-<2-(tert-Butyldimethylsiloxy)-4-methylphenyl>-2-cyclopropylideneethanol

There total 7 articles about 2-<2-(tert-Butyldimethylsiloxy)-4-methylphenyl>-2-cyclopropylideneethanol 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: 100.0%

: 154699-02-2
2-<2-(tert-Butyldimethylsiloxy)-4-methylphenyl>-2-cyclopropylideneethyl pivalate

: 154699-03-3
2-<2-(tert-Butyldimethylsiloxy)-4-methylphenyl>-2-cyclopropylideneethanol

Guidance literature:: With diisobutylaluminium hydride; In hexane; dichloromethane; at -23 ℃; for 0.5h;
DOI:10.1021/jo00080a014

Reference yield:

: 57234-27-2
1-(methoxymethoxy)-3-methylbenzene

: 154699-03-3
2-<2-(tert-Butyldimethylsiloxy)-4-methylphenyl>-2-cyclopropylideneethanol

Guidance literature:: Multi-step reaction with 7 steps

1: 80 percent / t-BuLi / diethyl ether; hexane / 0 °C / 1.) 2 h, 2.) 1 h

2: 94 percent / NaH / tris<2-(2-methoxyethoxy)ethyl>amine / tetrahydrofuran / 62 °C / 1.) 10 h, 2.) 1 h

3: 91 percent / EtSH, BF₃*Et₂O / CH₂Cl₂ / 1.) -78 deg C, 30 min, 2.) -23 deg C, 1.5 h

4: 99 percent / n-Bu₄N⁽¹⁺⁾*F^(1-) / tetrahydrofuran / 1 h / Ambient temperature

5: 85 percent / pyridine / 2 h / Ambient temperature

6: 86 percent / imidazole, DMAP / dimethylformamide / 10 h / 0 °C

7: 100 percent / DIBAL / CH₂Cl₂; hexane / 0.5 h / -23 °C

With pyridine; 1H-imidazole; dmap; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium hydride; diisobutylaluminium hydride; ethanethiol; Tris(3,6-dioxaheptyl)amine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00080a014

Reference yield:

: 154698-94-9
(tert-Butyldiphenylsiloxy)methyl 2-<(methoxymethyl)oxy>-4-methylphenyl ketone

: 154699-03-3
2-<2-(tert-Butyldimethylsiloxy)-4-methylphenyl>-2-cyclopropylideneethanol

Guidance literature:: Multi-step reaction with 6 steps

1: 94 percent / NaH / tris<2-(2-methoxyethoxy)ethyl>amine / tetrahydrofuran / 62 °C / 1.) 10 h, 2.) 1 h

2: 91 percent / EtSH, BF₃*Et₂O / CH₂Cl₂ / 1.) -78 deg C, 30 min, 2.) -23 deg C, 1.5 h

3: 99 percent / n-Bu₄N⁽¹⁺⁾*F^(1-) / tetrahydrofuran / 1 h / Ambient temperature

4: 85 percent / pyridine / 2 h / Ambient temperature

5: 86 percent / imidazole, DMAP / dimethylformamide / 10 h / 0 °C

6: 100 percent / DIBAL / CH₂Cl₂; hexane / 0.5 h / -23 °C

With pyridine; 1H-imidazole; dmap; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; ethanethiol; Tris(3,6-dioxaheptyl)amine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00080a014