ethyl 1-methyl-4-hydroxy-2-(4-trimethylsilylfuran-3-yl)methylcyclohex-2-ene-1-carboxylate

Base Information

Chemical Name:ethyl 1-methyl-4-hydroxy-2-(4-trimethylsilylfuran-3-yl)methylcyclohex-2-ene-1-carboxylate
CAS No.:503624-17-7
Molecular Formula:C₁₈H₂₈O₄Si
Molecular Weight:336.503
Hs Code.:

Synonyms:ethyl 1-methyl-4-hydroxy-2-(4-trimethylsilylfuran-3-yl)methylcyclohex-2-ene-1-carboxylate

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Chemical Property of ethyl 1-methyl-4-hydroxy-2-(4-trimethylsilylfuran-3-yl)methylcyclohex-2-ene-1-carboxylate

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Technology Process of ethyl 1-methyl-4-hydroxy-2-(4-trimethylsilylfuran-3-yl)methylcyclohex-2-ene-1-carboxylate

There total 6 articles about ethyl 1-methyl-4-hydroxy-2-(4-trimethylsilylfuran-3-yl)methylcyclohex-2-ene-1-carboxylate 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: 92.0%

: 503624-16-6
ethyl 1-methyl-4-oxo-2-(4-trimethylsilylfuran-3-yl)methylcyclohex-2-ene-1-carboxylate

: 503624-17-7
ethyl 1-methyl-4-hydroxy-2-(4-trimethylsilylfuran-3-yl)methylcyclohex-2-ene-1-carboxylate

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride; In ethanol; for 0.5h;
DOI:10.1016/S0040-4020(02)01519-3

Reference yield:

: 28790-87-6
ethyl 1,2-dimethyl-4-oxocyclohex-2-ene-1-carboxylate

: 503624-17-7
ethyl 1-methyl-4-hydroxy-2-(4-trimethylsilylfuran-3-yl)methylcyclohex-2-ene-1-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: 80 percent / pyridinium bromide perbromide / acetic acid / 3 h / 20 °C

2: 100 percent / p-TsOH / benzene / 48 h / Heating

3: 70 percent / Pd(PPh₃)4; aq. K₃PO₄ / tetrahydrofuran / 3 h / Heating

4: 65 percent / aq. AcOH / 2 h / 80 °C

5: 94 percent / Zn; AcOH / 0.5 h

6: 92 percent / CeCl₃; NaBH₄ / ethanol / 0.5 h

With sodium tetrahydroborate; potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; cerium(III) chloride; pyridinium hydrobromide perbromide; toluene-4-sulfonic acid; acetic acid; zinc; In tetrahydrofuran; ethanol; acetic acid; benzene; 3: Suzuki coupling;
DOI:10.1016/S0040-4020(02)01519-3

Reference yield:

: 503624-12-2
ethyl 5-bromo-2-bromomethyl-1-methyl-4-oxocyclohex-2-ene-1-carboxylate

: 503624-17-7
ethyl 1-methyl-4-hydroxy-2-(4-trimethylsilylfuran-3-yl)methylcyclohex-2-ene-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / p-TsOH / benzene / 48 h / Heating

2: 70 percent / Pd(PPh₃)4; aq. K₃PO₄ / tetrahydrofuran / 3 h / Heating

3: 65 percent / aq. AcOH / 2 h / 80 °C

4: 94 percent / Zn; AcOH / 0.5 h

5: 92 percent / CeCl₃; NaBH₄ / ethanol / 0.5 h

With sodium tetrahydroborate; potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; cerium(III) chloride; toluene-4-sulfonic acid; acetic acid; zinc; In tetrahydrofuran; ethanol; benzene; 2: Suzuki coupling;
DOI:10.1016/S0040-4020(02)01519-3