2-[(2'E)-6'-tert-butyldimethylsilyloxy-3'-methyl-2'-hexen-1'-yl]-6-methyl-1,4-hydroquinone 1,4-dimethyl ether

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Chemical Name:2-[(2'E)-6'-tert-butyldimethylsilyloxy-3'-methyl-2'-hexen-1'-yl]-6-methyl-1,4-hydroquinone 1,4-dimethyl ether
CAS No.:890527-13-6
Molecular Formula:C₂₄H₄₂O₅Si
Molecular Weight:438.68
Hs Code.:

Synonyms:2-[(2'E)-6'-tert-butyldimethylsilyloxy-3'-methyl-2'-hexen-1'-yl]-6-methyl-1,4-hydroquinone 1,4-dimethyl ether

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Chemical Property of 2-[(2'E)-6'-tert-butyldimethylsilyloxy-3'-methyl-2'-hexen-1'-yl]-6-methyl-1,4-hydroquinone 1,4-dimethyl ether

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Technology Process of 2-[(2'E)-6'-tert-butyldimethylsilyloxy-3'-methyl-2'-hexen-1'-yl]-6-methyl-1,4-hydroquinone 1,4-dimethyl ether

There total 8 articles about 2-[(2'E)-6'-tert-butyldimethylsilyloxy-3'-methyl-2'-hexen-1'-yl]-6-methyl-1,4-hydroquinone 1,4-dimethyl ether 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: 75.0%

: 50848-61-8
1-bromo-2,5-bis(methoxymethoxy)-3-methylbenzene

: 118607-92-4
6-bromo-4-methyl-4(E)-hexenyl tert-butyldimethylsilyl ether

: 890527-13-6
2-[(2'E)-6'-tert-butyldimethylsilyloxy-3'-methyl-2'-hexen-1'-yl]-6-methyl-1,4-hydroquinone 1,4-dimethyl ether

Guidance literature:: 1-bromo-2,5-bis(methoxymethoxy)-3-methylbenzene; With n-butyllithium; In diethyl ether; hexane; at -78 ℃; for 1h;

With CuI*P(n-Bu)3; In diethyl ether; hexane; at -60 ℃; for 1.25h;

6-bromo-4-methyl-4(E)-hexenyl tert-butyldimethylsilyl ether; In diethyl ether; hexane; at -60 - 0 ℃; for 2.33333h;
DOI:10.1248/cpb.54.391

Reference yield:

: 105-87-3,8022-83-1
3,7-dimethyl-2E,6-octadien-1-yl acetate

: 890527-13-6
2-[(2'E)-6'-tert-butyldimethylsilyloxy-3'-methyl-2'-hexen-1'-yl]-6-methyl-1,4-hydroquinone 1,4-dimethyl ether

Guidance literature:: Multi-step reaction with 8 steps

1.1: 47 percent / K₂CO₃; K₃Fe(CN)6; K₂OsO₄ / 2-methyl-propan-2-ol; H₂O / 72 h / 4 °C

2.1: 98 percent / aq. NaIO₄ / acetone / 0 - 20 °C

3.1: 99 percent / NaBH₄ / methanol / 0 °C

4.1: 100 percent / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 4 h / 20 °C

5.1: 100 percent / K₂CO₃ / methanol / 1 h / 0 °C

6.1: methanesulfonyl chloride; Et₃N / CHCl₃ / 0.5 h / 0 °C

7.1: lithium bromide / dimethylformamide / 1 h / 20 °C

8.1: BuLi / diethyl ether; hexane / 1 h / -78 °C

8.2: CuI*PBu₃ / diethyl ether; hexane / 1.25 h / -60 °C

8.3: 75 percent / diethyl ether; hexane / 2.33 h / -60 - 0 °C

With dmap; sodium tetrahydroborate; potassium osmate(VI); sodium periodate; n-butyllithium; potassium carbonate; methanesulfonyl chloride; triethylamine; lithium bromide; potassium hexacyanoferrate(III); In methanol; diethyl ether; hexane; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
DOI:10.1248/cpb.54.391

Reference yield:

: 35334-60-2
(E)-6-acetoxy-4-methyl-4-hexenal

: 890527-13-6
2-[(2'E)-6'-tert-butyldimethylsilyloxy-3'-methyl-2'-hexen-1'-yl]-6-methyl-1,4-hydroquinone 1,4-dimethyl ether

Guidance literature:: Multi-step reaction with 6 steps

1.1: 99 percent / NaBH₄ / methanol / 0 °C

2.1: 100 percent / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 4 h / 20 °C

3.1: 100 percent / K₂CO₃ / methanol / 1 h / 0 °C

4.1: methanesulfonyl chloride; Et₃N / CHCl₃ / 0.5 h / 0 °C

5.1: lithium bromide / dimethylformamide / 1 h / 20 °C

6.1: BuLi / diethyl ether; hexane / 1 h / -78 °C

6.2: CuI*PBu₃ / diethyl ether; hexane / 1.25 h / -60 °C

6.3: 75 percent / diethyl ether; hexane / 2.33 h / -60 - 0 °C

With dmap; sodium tetrahydroborate; n-butyllithium; potassium carbonate; methanesulfonyl chloride; triethylamine; lithium bromide; In methanol; diethyl ether; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1248/cpb.54.391