4-[(5R,6R)-5-Isopropenyl-6-(2-methoxy-ethoxymethoxy)-2-methyl-cyclohex-2-en-(E)-ylidene]-2,2-dimethyl-butyric acid

Base Information

Chemical Name:4-[(5R,6R)-5-Isopropenyl-6-(2-methoxy-ethoxymethoxy)-2-methyl-cyclohex-2-en-(E)-ylidene]-2,2-dimethyl-butyric acid
CAS No.:423764-41-4
Molecular Formula:C₂₀H₃₂O₅
Molecular Weight:352.471
Hs Code.:

Synonyms:4-[(5R,6R)-5-Isopropenyl-6-(2-methoxy-ethoxymethoxy)-2-methyl-cyclohex-2-en-(E)-ylidene]-2,2-dimethyl-butyric acid

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Chemical Property of 4-[(5R,6R)-5-Isopropenyl-6-(2-methoxy-ethoxymethoxy)-2-methyl-cyclohex-2-en-(E)-ylidene]-2,2-dimethyl-butyric acid

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Technology Process of 4-[(5R,6R)-5-Isopropenyl-6-(2-methoxy-ethoxymethoxy)-2-methyl-cyclohex-2-en-(E)-ylidene]-2,2-dimethyl-butyric acid

There total 5 articles about 4-[(5R,6R)-5-Isopropenyl-6-(2-methoxy-ethoxymethoxy)-2-methyl-cyclohex-2-en-(E)-ylidene]-2,2-dimethyl-butyric acid 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:

: 423764-40-3
Isobutyric acid (1S,5R,6R)-5-isopropenyl-6-(2-methoxy-ethoxymethoxy)-2-methyl-1-vinyl-cyclohex-2-enyl ester

: 423764-41-4
4-[(5R,6R)-5-Isopropenyl-6-(2-methoxy-ethoxymethoxy)-2-methyl-cyclohex-2-en-(E)-ylidene]-2,2-dimethyl-butyric acid

Guidance literature:: Isobutyric acid (1S,5R,6R)-5-isopropenyl-6-(2-methoxy-ethoxymethoxy)-2-methyl-1-vinyl-cyclohex-2-enyl ester; With triisopropylsilyl trifluoromethanesulfonate; potassium hexamethylsilazane; In diethyl ether; toluene; at -78 - 20 ℃;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 3h; Further stages.;
DOI:10.1021/jo010752r

Reference yield:

: 423764-68-5
(1R,2S,6R)-6-Isopropenyl-3-methyl-2-vinyl-cyclohex-3-ene-1,2-diol

: 423764-41-4
4-[(5R,6R)-5-Isopropenyl-6-(2-methoxy-ethoxymethoxy)-2-methyl-cyclohex-2-en-(E)-ylidene]-2,2-dimethyl-butyric acid

Guidance literature:: Multi-step reaction with 3 steps

1.1: 60 percent / ethyldiisopropylamine / CH₂Cl₂ / 16 h / 20 °C

2.1: CH₂=CHMgBr / tetrahydrofuran / 1 h / 20 °C

2.2: 60 percent / tetrahydrofuran / 10 h / 20 °C

3.1: KHMDS; TIPSOTf / diethyl ether; toluene / -78 - 20 °C

3.2: Bu₄NF / tetrahydrofuran / 3 h / 0 °C

With vinyl magnesium bromide; triisopropylsilyl trifluoromethanesulfonate; potassium hexamethylsilazane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1021/jo010752r

Reference yield:

: 423764-38-9
(5R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-5-isopropenyl-2-methyl-cyclohex-2-enone

: 423764-41-4
4-[(5R,6R)-5-Isopropenyl-6-(2-methoxy-ethoxymethoxy)-2-methyl-cyclohex-2-en-(E)-ylidene]-2,2-dimethyl-butyric acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-BuLi / tetrahydrofuran / 1 h / 20 °C

1.2: 70 percent / tetrahydrofuran / 6 h / 20 °C

2.1: 90 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

3.1: 60 percent / ethyldiisopropylamine / CH₂Cl₂ / 16 h / 20 °C

4.1: CH₂=CHMgBr / tetrahydrofuran / 1 h / 20 °C

4.2: 60 percent / tetrahydrofuran / 10 h / 20 °C

5.1: KHMDS; TIPSOTf / diethyl ether; toluene / -78 - 20 °C

5.2: Bu₄NF / tetrahydrofuran / 3 h / 0 °C

With n-butyllithium; vinyl magnesium bromide; tetrabutyl ammonium fluoride; triisopropylsilyl trifluoromethanesulfonate; potassium hexamethylsilazane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1021/jo010752r