5-t-butyldimethylsilyloxy-3-(3'-hydroxy-3'-methylpent-4'-enyl)-2,4,4-trimethylcyclohex-2-enone

Base Information

Chemical Name:5-t-butyldimethylsilyloxy-3-(3'-hydroxy-3'-methylpent-4'-enyl)-2,4,4-trimethylcyclohex-2-enone
CAS No.:302329-72-2
Molecular Formula:C₂₁H₃₈O₃Si
Molecular Weight:366.616
Hs Code.:

Synonyms:5-t-butyldimethylsilyloxy-3-(3'-hydroxy-3'-methylpent-4'-enyl)-2,4,4-trimethylcyclohex-2-enone

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Chemical Property of 5-t-butyldimethylsilyloxy-3-(3'-hydroxy-3'-methylpent-4'-enyl)-2,4,4-trimethylcyclohex-2-enone

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Technology Process of 5-t-butyldimethylsilyloxy-3-(3'-hydroxy-3'-methylpent-4'-enyl)-2,4,4-trimethylcyclohex-2-enone

There total 12 articles about 5-t-butyldimethylsilyloxy-3-(3'-hydroxy-3'-methylpent-4'-enyl)-2,4,4-trimethylcyclohex-2-enone 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: 87.0%

: 1826-67-1
vinyl magnesium bromide

: 302329-70-0
5-t-butyldimethylsilyloxy-3-(3'-oxobutyl)-2,4,4-trimethylcyclohex-2-enone

: 302329-72-2
5-t-butyldimethylsilyloxy-3-(3'-hydroxy-3'-methylpent-4'-enyl)-2,4,4-trimethylcyclohex-2-enone

Guidance literature:: In tetrahydrofuran; at 0 ℃; for 0.75h;
DOI:10.1016/S0040-4020(00)00560-3

Reference yield:

: (2',5'-epoxy-2',6',6'-trimethyl) cyclohexylmethyl tosylate

: 302329-72-2
5-t-butyldimethylsilyloxy-3-(3'-hydroxy-3'-methylpent-4'-enyl)-2,4,4-trimethylcyclohex-2-enone

Guidance literature:: Multi-step reaction with 12 steps

1.1: KH / ethanol / 0.25 h

1.2: 92 percent / ethanol / 4 h / Heating

2.1: 98 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / 20 °C

3.1: n-BuLi; HMPA / tetrahydrofuran; hexane / -78 - 0 °C

3.2: 77 percent / dimethylsulfoxide; hexane / 12 h / -78 °C

4.1: m-chloroperbenzoic acid / CH₂Cl₂ / 77 h / 20 °C

5.1: 98 percent / LiAlH₄ / tetrahydrofuran

6.1: 95 percent / pyridine / 6 h / 20 °C

7.1: 89 percent / BBr₃ / CH₂Cl₂ / 0.25 h / 20 °C

8.1: 95 percent / imidazole; DMAP / dimethylformamide / 44 h / 20 °C

9.1: 88 percent / Na₂CrO₄; NaOAc / benzene; acetic anhydride; acetic acid / 3 h / 65 °C

10.1: 95 percent / K₂CO₃ / methanol / 1 h / 20 °C

11.1: 96 percent / Jones reagent / acetone / 0.5 h / -15 °C

12.1: 87 percent / tetrahydrofuran / 0.75 h / 0 °C

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; n-butyllithium; jones reagent; sodium chromate(VI); sodium acetate; boron tribromide; potassium hydride; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; acetic anhydride; acetic acid; N,N-dimethyl-formamide; acetone; benzene; 1.1: deprotonation / 1.2: Substitution / 2.1: Oxidation / 3.1: Metallation / 3.2: Substitution / 4.1: Epoxidation / 5.1: Ring cleavage / 6.1: Acetylation / 7.1: Ring cleavage / 8.1: Substitution / 9.1: Oxidation / 10.1: Deacetylation / 11.1: Oxidation / 12.1: Grignard reaction;
DOI:10.1016/S0040-4020(00)00560-3

Reference yield:

: 4-(2',5'-epoxy-2',6',6'-trimethyl)cyclohexyl-2-butanol

: 302329-72-2
5-t-butyldimethylsilyloxy-3-(3'-hydroxy-3'-methylpent-4'-enyl)-2,4,4-trimethylcyclohex-2-enone

Guidance literature:: Multi-step reaction with 7 steps

1: 95 percent / pyridine / 6 h / 20 °C

2: 89 percent / BBr₃ / CH₂Cl₂ / 0.25 h / 20 °C

3: 95 percent / imidazole; DMAP / dimethylformamide / 44 h / 20 °C

4: 88 percent / Na₂CrO₄; NaOAc / benzene; acetic anhydride; acetic acid / 3 h / 65 °C

5: 95 percent / K₂CO₃ / methanol / 1 h / 20 °C

6: 96 percent / Jones reagent / acetone / 0.5 h / -15 °C

7: 87 percent / tetrahydrofuran / 0.75 h / 0 °C

With pyridine; 1H-imidazole; dmap; jones reagent; sodium chromate(VI); sodium acetate; boron tribromide; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane; acetic anhydride; acetic acid; N,N-dimethyl-formamide; acetone; benzene; 1: Acetylation / 2: Ring cleavage / 3: Substitution / 4: Oxidation / 5: Deacetylation / 6: Oxidation / 7: Grignard reaction;
DOI:10.1016/S0040-4020(00)00560-3