diethyl 1-[2-(5-hydroxypent-3-ynyl)-5,5-dimethyl-3-oxocyclohex-1-enyl]propa-1,2-dienylphosphonate

Base Information

Chemical Name:diethyl 1-[2-(5-hydroxypent-3-ynyl)-5,5-dimethyl-3-oxocyclohex-1-enyl]propa-1,2-dienylphosphonate
CAS No.:1418184-21-0
Molecular Formula:C₂₀H₂₉O₅P
Molecular Weight:380.421
Hs Code.:

Synonyms:diethyl 1-[2-(5-hydroxypent-3-ynyl)-5,5-dimethyl-3-oxocyclohex-1-enyl]propa-1,2-dienylphosphonate

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Chemical Property of diethyl 1-[2-(5-hydroxypent-3-ynyl)-5,5-dimethyl-3-oxocyclohex-1-enyl]propa-1,2-dienylphosphonate

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Technology Process of diethyl 1-[2-(5-hydroxypent-3-ynyl)-5,5-dimethyl-3-oxocyclohex-1-enyl]propa-1,2-dienylphosphonate

There total 5 articles about diethyl 1-[2-(5-hydroxypent-3-ynyl)-5,5-dimethyl-3-oxocyclohex-1-enyl]propa-1,2-dienylphosphonate 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: 62.0%

: 1426540-07-9
C₂₂H₃₁O₆P

: 1418184-21-0
diethyl 1-[2-(5-hydroxypent-3-ynyl)-5,5-dimethyl-3-oxocyclohex-1-enyl]propa-1,2-dienylphosphonate

Guidance literature:: With potassium carbonate; In methanol; for 0.0833333h; Inert atmosphere;
DOI:10.1016/j.tet.2012.12.014

Reference yield:

: 1418184-10-7
2-allyl-3-hydroxy-5,5-dimethylcyclohex-1-enyl trifluoromethanesulfonate

: 1418184-21-0
diethyl 1-[2-(5-hydroxypent-3-ynyl)-5,5-dimethyl-3-oxocyclohex-1-enyl]propa-1,2-dienylphosphonate

Guidance literature:: Multi-step reaction with 8 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

1.2: 1.5 h / 0 - 20 °C / Inert atmosphere

2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 3.5 h / 20 °C / Inert atmosphere

2.2: Ohira-Bestmann reagent / 20 °C / Inert atmosphere

3.1: ethylmagnesium bromide / tetrahydrofuran / 2 h / 0 - 50 °C / Inert atmosphere

3.2: 20 °C / Inert atmosphere

4.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

5.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere

6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 5.5 h / 20 °C / Inert atmosphere

6.2: 2 h / 20 °C / Inert atmosphere

7.1: triethylamine / tetrahydrofuran / 9.5 h / -78 °C / Reflux; Inert atmosphere

8.1: potassium carbonate / methanol / 0.08 h / Inert atmosphere

With 1H-imidazole; dmap; ethylmagnesium bromide; tetrabutyl ammonium fluoride; potassium carbonate; acetic acid; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2012.12.014

Reference yield:

: 1418184-11-8
3-(tert-butyldimethylsilyloxy)-2-(3-hydroxypropyl)-5,5-dimethylcyclohex-1-enyl trifluoromethanesulfonate

: 1418184-21-0
diethyl 1-[2-(5-hydroxypent-3-ynyl)-5,5-dimethyl-3-oxocyclohex-1-enyl]propa-1,2-dienylphosphonate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 3.5 h / 20 °C / Inert atmosphere

1.2: Ohira-Bestmann reagent / 20 °C / Inert atmosphere

2.1: ethylmagnesium bromide / tetrahydrofuran / 2 h / 0 - 50 °C / Inert atmosphere

2.2: 20 °C / Inert atmosphere

3.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere

5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 5.5 h / 20 °C / Inert atmosphere

5.2: 2 h / 20 °C / Inert atmosphere

6.1: triethylamine / tetrahydrofuran / 9.5 h / -78 °C / Reflux; Inert atmosphere

7.1: potassium carbonate / methanol / 0.08 h / Inert atmosphere

With dmap; ethylmagnesium bromide; tetrabutyl ammonium fluoride; potassium carbonate; acetic acid; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1016/j.tet.2012.12.014