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

Base Information

Chemical Name:2-<2-(tert-Butyldimethylsiloxy)-4-methylphenyl>-2-cyclopropylideneethyl pivalate
CAS No.:154699-02-2
Molecular Formula:C₂₃H₃₆O₃Si
Molecular Weight:388.623
Hs Code.:

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

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

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

There total 7 articles about 2-<2-(tert-Butyldimethylsiloxy)-4-methylphenyl>-2-cyclopropylideneethyl pivalate 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: 86.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 154699-01-1
2-Cyclopropylidene-2-(2-hydroxy-4-methylphenyl)ethyl pivalate

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

Guidance literature:: With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 0 ℃; for 10h;
DOI:10.1021/jo00080a014

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 6 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

With pyridine; 1H-imidazole; dmap; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium 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

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

Guidance literature:: Multi-step reaction with 5 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

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