[1-(3-methyl-but-2-enyl)-2,6-dioxo-cyclohexyl]-acetic acid ethyl ester

Base Information

Chemical Name:[1-(3-methyl-but-2-enyl)-2,6-dioxo-cyclohexyl]-acetic acid ethyl ester
CAS No.:230976-10-0
Molecular Formula:C₁₅H₂₂O₄
Molecular Weight:266.337
Hs Code.:

Synonyms:[1-(3-methyl-but-2-enyl)-2,6-dioxo-cyclohexyl]-acetic acid ethyl ester

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Chemical Property of [1-(3-methyl-but-2-enyl)-2,6-dioxo-cyclohexyl]-acetic acid ethyl ester

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Technology Process of [1-(3-methyl-but-2-enyl)-2,6-dioxo-cyclohexyl]-acetic acid ethyl ester

There total 1 articles about [1-(3-methyl-but-2-enyl)-2,6-dioxo-cyclohexyl]-acetic acid ethyl ester 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: 80.0%

: 56946-66-8
2-(3-methylbut-2-en-1-yl)cyclohexane-1,3-dione

: 105-36-2
ethyl bromoacetate

: 230976-10-0
[1-(3-methyl-but-2-enyl)-2,6-dioxo-cyclohexyl]-acetic acid ethyl ester

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium iodide; In tetrahydrofuran; at 65 ℃; for 24h;
DOI:10.1021/ja9905445

Reference yield:

: 230976-10-0
[1-(3-methyl-but-2-enyl)-2,6-dioxo-cyclohexyl]-acetic acid ethyl ester

: 230976-11-1
[(1R,2S,6R)-2,6-Dihydroxy-1-(3-methyl-but-2-enyl)-cyclohexyl]-acetic acid ethyl ester

Guidance literature:: With lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; at 0 ℃; for 2.5h;
DOI:10.1021/ja9905445

Reference yield:

: 230976-10-0
[1-(3-methyl-but-2-enyl)-2,6-dioxo-cyclohexyl]-acetic acid ethyl ester

: C₂₉H₃₈O₈S

Guidance literature:: Multi-step reaction with 22 steps

1: LiAlH(O-t-Bu)3 / tetrahydrofuran / 2.5 h / 0 °C

2: aq. LiOH / tetrahydrofuran / 0.5 h / 25 °C

3: DCC, 4-DMAP / CH₂Cl₂ / 0.5 h / 25 °C

4: 77 percent / PDC, celite / CH₂Cl₂ / 6 h / 25 °C

5: LHMDS, HMPA / tetrahydrofuran / 0.5 h / -78 °C

6: DMAP / 1 h / 70 °C

7: 95 percent / SnCl₄ / CH₂Cl₂ / 0.25 h / -23 °C

8: 95 percent / LiAlH(O-t-Bu)3 / tetrahydrofuran / 2.5 h / 0 - 25 °C

9: 82 percent / LHMDS / tetrahydrofuran / 2.5 h / 0 - 25 °C

10: 93 percent / n-Bu₃SnH, AIBN / benzene / 12 h / 80 °C

11: 80 percent / DIBAL / CH₂Cl₂ / 12 h / -78 - 25 °C

12: 89 percent / 4-DMAP, pyridine / 12 h / 25 °C

13: TEMPO, Phl(OAc)2 / CH₂Cl₂ / 5 h / 25 °C

14: tetrahydrofuran / 12 h / -78 - 25 °C

15: 73 percent / H₂ / PtO₂ / ethanol / 72 h / 25 °C

16: 86 percent / pyridine / CH₂Cl₂ / 0.5 h / -78 - 25 °C

17: 88 percent / H₂ / Pd/C / ethanol / 24 h / 25 °C

18: 87 percent / tetrapropylammonium perruthenate, 4-methylmorpholine N-oxide, 4 Angstroem MS / CH₂Cl₂ / 12 h / 25 °C

19: 60 percent / SeO₂, AcOH / 1 h / 110 °C

20: 44 percent / benzene / 8 h / 25 °C / Irradiation

21: 82 percent / H₂SO₄ / diethyl ether / 12 h / 25 °C

22: 86 percent / TsOH / 25 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; lithium hydroxide; dipyridinium dichromate; selenium(IV) oxide; tetrapropylammonium perruthennate; 2,2'-azobis(isobutyronitrile); [bis(acetoxy)iodo]benzene; 4 Angstroem MS; Celite; sulfuric acid; hydrogen; tri-n-butyl-tin hydride; tin(IV) chloride; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; 4-methylmorpholine N-oxide; lithium tri-t-butoxyaluminum hydride; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; benzene;
DOI:10.1021/ja9905445