[2,5-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-(5,8-dihydroxy-2,2-dimethyl-2H-chromen-6-yl)-methanone

Base Information

Chemical Name:[2,5-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-(5,8-dihydroxy-2,2-dimethyl-2H-chromen-6-yl)-methanone
CAS No.:557757-37-6
Molecular Formula:C₃₀H₄₄O₆Si₂
Molecular Weight:556.847
Hs Code.:

[2,5-bis-(<i>tert</i>-butyl-dimethyl-silanyloxy)-phenyl]-(5,8-dihydroxy-2,2-dimethyl-2<i>H</i>-chromen-6-yl)-methanone

Synonyms:[2,5-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-(5,8-dihydroxy-2,2-dimethyl-2H-chromen-6-yl)-methanone

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Chemical Property of [2,5-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-(5,8-dihydroxy-2,2-dimethyl-2H-chromen-6-yl)-methanone

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Technology Process of [2,5-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-(5,8-dihydroxy-2,2-dimethyl-2H-chromen-6-yl)-methanone

There total 13 articles about [2,5-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-(5,8-dihydroxy-2,2-dimethyl-2H-chromen-6-yl)-methanone 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: 70.0%

: 557757-36-5
[2,5-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-[5,8-bis-(2-methoxy-ethoxymethoxy)-2,2-dimethyl-2H-chromen-6-yl]-methanone

: 557757-37-6
[2,5-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-(5,8-dihydroxy-2,2-dimethyl-2H-chromen-6-yl)-methanone

Guidance literature:: With zinc dibromide; In dichloromethane; at 25 ℃; for 4h;
DOI:10.1016/S0040-4039(03)00629-4

Reference yield:

: 31558-41-5
4-bromo-2,5-dimethoxybenzaldehyde

: 557757-37-6
[2,5-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-(5,8-dihydroxy-2,2-dimethyl-2H-chromen-6-yl)-methanone

Guidance literature:: Multi-step reaction with 9 steps

1.1: m-CPBA / CH₂Cl₂ / 4 h / 25 °C

1.2: 99 percent / aq. NaOH / methanol / 1 h / 25 °C

2.1: 84 percent / DBU; CuCl₂ / acetonitrile / 6 h / 0 °C

3.1: cerium ammonium nitrate / acetonitrile; H₂O / 0.5 h / 25 °C

4.1: PhCH₃ / 0.5 h / 40 °C

5.1: NaBH₄; AcOH / tetrahydrofuran / 0.5 h / 25 °C

6.1: DIPEA / CH₂Cl₂ / 2 h / 0 °C

7.1: 52 percent / n-BuLi / diethyl ether / 1 h / -78 - 0 °C

8.1: 66 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 25 °C

9.1: 70 percent / ZnBr₂ / CH₂Cl₂ / 4 h / 25 °C

With sodium tetrahydroborate; n-butyllithium; ammonium cerium(IV) nitrate; Dess-Martin periodane; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; toluene; copper dichloride; zinc dibromide; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetonitrile; 1.1: Baeyer-Villiger oxidation / 4.1: Claisen cyclization;
DOI:10.1016/S0040-4039(03)00629-4

Reference yield:

: 1194-98-5
2,5-Dihydroxybenzaldehyde

: 557757-37-6
[2,5-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-(5,8-dihydroxy-2,2-dimethyl-2H-chromen-6-yl)-methanone

Guidance literature:: Multi-step reaction with 4 steps

1: 62 percent / imid / CH₂Cl₂ / 4 h / 25 °C

2: 52 percent / n-BuLi / diethyl ether / 1 h / -78 - 0 °C

3: 66 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 25 °C

4: 70 percent / ZnBr₂ / CH₂Cl₂ / 4 h / 25 °C

With 1H-imidazole; n-butyllithium; Dess-Martin periodane; zinc dibromide; In diethyl ether; dichloromethane;
DOI:10.1016/S0040-4039(03)00629-4