(S,Z)-2-methyl-2-(4-methyl-3,6-dioxocyclohexa-1,4-dienyloxy)-7-(trimethylsilyl)hept-5-en-3-yl acetate

Base Information

Chemical Name:(S,Z)-2-methyl-2-(4-methyl-3,6-dioxocyclohexa-1,4-dienyloxy)-7-(trimethylsilyl)hept-5-en-3-yl acetate
CAS No.:1398242-83-5
Molecular Formula:C₂₀H₃₀O₅Si
Molecular Weight:378.541
Hs Code.:

Synonyms:(S,Z)-2-methyl-2-(4-methyl-3,6-dioxocyclohexa-1,4-dienyloxy)-7-(trimethylsilyl)hept-5-en-3-yl acetate

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Chemical Property of (S,Z)-2-methyl-2-(4-methyl-3,6-dioxocyclohexa-1,4-dienyloxy)-7-(trimethylsilyl)hept-5-en-3-yl acetate

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Technology Process of (S,Z)-2-methyl-2-(4-methyl-3,6-dioxocyclohexa-1,4-dienyloxy)-7-(trimethylsilyl)hept-5-en-3-yl acetate

There total 7 articles about (S,Z)-2-methyl-2-(4-methyl-3,6-dioxocyclohexa-1,4-dienyloxy)-7-(trimethylsilyl)hept-5-en-3-yl acetate 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: 97.0%

: 1398245-45-8
(S,Z)-2-(2,5-dimethoxy-4-methylphenoxy)-2-methyl-7-(trimethylsilyl)hept-5-en-3-yl acetate

: 1398242-83-5
(S,Z)-2-methyl-2-(4-methyl-3,6-dioxocyclohexa-1,4-dienyloxy)-7-(trimethylsilyl)hept-5-en-3-yl acetate

Guidance literature:: With ammonium cerium (IV) nitrate; In water; acetonitrile; at 0 ℃; for 0.0833333h;
DOI:10.1021/jo3016055

Reference yield:

: 4925-88-6
2,5-dimethoxy-4-methylbenzaldehyde

: 1398242-83-5
(S,Z)-2-methyl-2-(4-methyl-3,6-dioxocyclohexa-1,4-dienyloxy)-7-(trimethylsilyl)hept-5-en-3-yl acetate

Guidance literature:: Multi-step reaction with 9 steps

1.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / -10 °C / Inert atmosphere

1.2: 0.5 h / 20 °C / Inert atmosphere

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 3.5 h / 20 °C / Inert atmosphere

3.1: hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; potassium hexacyanoferrate(III); potassium carbonate; potassium dioxido(dioxo)osmium hydrate; methanesulfonamide / water; tert-butyl alcohol / 19 h / 0 °C

4.1: triethylamine; dmap / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

5.1: potassium carbonate / methanol / 1 h / 20 °C / Inert atmosphere

6.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

6.2: 0.17 h / -78 °C / Inert atmosphere

6.3: 1 h / -78 °C / Inert atmosphere

7.1: quinoline; hydrogen / ethyl acetate / 1 h / 50 °C

8.1: dmap; pyridine / dichloromethane / 5.5 h / 20 °C

9.1: ammonium cerium (IV) nitrate / water; acetonitrile / 0.08 h / 0 °C

With pyridine; quinoline; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; ammonium cerium (IV) nitrate; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; methanesulfonamide; potassium dioxido(dioxo)osmium hydrate; potassium hexacyanoferrate(III); hydrogen; sodium hydrogencarbonate; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo3016055

Reference yield:

: 24599-58-4
2,5-dimethoxy toluene

: 1398242-83-5
(S,Z)-2-methyl-2-(4-methyl-3,6-dioxocyclohexa-1,4-dienyloxy)-7-(trimethylsilyl)hept-5-en-3-yl acetate

Guidance literature:: Multi-step reaction with 10 steps

1.1: trichlorophosphate / 0.83 h / 20 °C / Inert atmosphere

1.2: 1 h / 70 °C / Inert atmosphere

2.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / -10 °C / Inert atmosphere

2.2: 0.5 h / 20 °C / Inert atmosphere

3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 3.5 h / 20 °C / Inert atmosphere

4.1: hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; potassium hexacyanoferrate(III); potassium carbonate; potassium dioxido(dioxo)osmium hydrate; methanesulfonamide / water; tert-butyl alcohol / 19 h / 0 °C

5.1: triethylamine; dmap / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

6.1: potassium carbonate / methanol / 1 h / 20 °C / Inert atmosphere

7.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

7.2: 0.17 h / -78 °C / Inert atmosphere

7.3: 1 h / -78 °C / Inert atmosphere

8.1: quinoline; hydrogen / ethyl acetate / 1 h / 50 °C

9.1: dmap; pyridine / dichloromethane / 5.5 h / 20 °C

10.1: ammonium cerium (IV) nitrate / water; acetonitrile / 0.08 h / 0 °C

With pyridine; quinoline; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; ammonium cerium (IV) nitrate; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; methanesulfonamide; potassium dioxido(dioxo)osmium hydrate; potassium hexacyanoferrate(III); hydrogen; sodium hydrogencarbonate; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; trichlorophosphate; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo3016055