methyl 6-(2,2,2-trichloroethoxycarbonyloxy)cyclohex-1-enoate

Base Information

• Chemical Name: methyl 6-(2,2,2-trichloroethoxycarbonyloxy)cyclohex-1-enoate
• CAS No.: 312920-36-8
• Molecular Formula: C₁₁H₁₃Cl₃O₅
• Molecular Weight: 331.58
• Mol file: 312920-36-8.mol

Synonyms:methyl 6-(2,2,2-trichloroethoxycarbonyloxy)cyclohex-1-enoate

Chemical Property of methyl 6-(2,2,2-trichloroethoxycarbonyloxy)cyclohex-1-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 6-(2,2,2-trichloroethoxycarbonyloxy)cyclohex-1-enoate

There total 1 articles about methyl 6-(2,2,2-trichloroethoxycarbonyloxy)cyclohex-1-enoate 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: 93.0%

methyl 6-hydroxy-cyclohex-1-enecarboxylate (865780-25-2) + 2,2,2-Trichloroethyl chloroformate (17341-93-4) → methyl 6-(2,2,2-trichloroethoxycarbonyloxy)cyclohex-1-enoate (312920-36-8)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/ja054449+

Reference yield:

methyl 6-(2,2,2-trichloroethoxycarbonyloxy)cyclohex-1-enoate (312920-36-8) → MORPHIN (57-27-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: [(ν³-C3H5)PdCl]2; (1S,2S)-bis(N,N'-(o-(PPh2)C6H4CO)-1,2-diphenylethylamine; Et3N / CH2Cl2 / 8 h / 20 °C

2.1: TsOH*H₂O / methanol / 4 h / 50 °C

3.1: DIBAlH / toluene; hexane / 1.5 h / -78 °C

4.1: Ph₃P; diisopropylazodicarboxylate / diethyl ether / 0.33 h / -20 °C

4.2: diethyl ether / 12 h / -20 - 20 °C

4.3: 1.34 g / aq. TsOH / tetrahydrofuran / 4 h / 20 °C

5.1: 91 percent / Pd(OAc)2; Ag₂CO₃; diphenylphosphinopropane / 1,3-bis(diphenylphosphino)propane / toluene / 24 h / 107 °C

6.1: 91 percent / PPh₃ / CH₂Cl₂ / 0.17 h / 0 °C

7.1: 88 percent / Pd(PPh₃)4; Bu₃SnH / toluene / 0.33 h

8.1: 65 percent / Pd(OAc)2; Ag₂CO₃; diphenylphosphinopropane / 1,3-bis(diphenylphosphino)propane / toluene / 4 h / 107 °C

9.1: SeO₂; quartz sand / dioxane / 1.33 h / 75 °C

10.1: DIBALH / CH₂Cl₂; hexane; diethyl ether / -78 - 0 °C

10.2: NH₄Br / various solvents / 2 h / 20 °C

10.3: 89 percent / NaBH₄ / various solvents / 20 °C

11.1: LDA / tetrahydrofuran; hexane / -78 - 20 °C

11.2: 57 percent / tetrahydrofuran; hexane / 6 h / 20 °C / Irradiation

12.1: BBr₃

With palladium diacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; selenium(IV) oxide; di-isopropyl azodicarboxylate; [(ν³-allyl)PdCl]2; tri-n-butyl-tin hydride; boron tribromide; diisobutylaluminium hydride; toluene-4-sulfonic acid; (+)-1(S),2(S)-bis<2'-(diphenylphosphino)benzamido>-1,2-diphenylethane; triethylamine; triphenylphosphine; diphenylphosphinopropane; silver carbonate; lithium diisopropyl amide; 1,3-bis-(diphenylphosphino)propane; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; dichloromethane; toluene; 4.2: Mitsunobu reaction / 5.1: Heck reaction;

DOI:10.1021/ja054449+

Reference yield:

methyl 6-(2,2,2-trichloroethoxycarbonyloxy)cyclohex-1-enoate (312920-36-8) → codeine (76-57-3)

Guidance literature:

Multi-step reaction with 11 steps

1.1: [(ν³-C3H5)PdCl]2; (1S,2S)-bis(N,N'-(o-(PPh2)C6H4CO)-1,2-diphenylethylamine; Et3N / CH2Cl2 / 8 h / 20 °C

2.1: TsOH*H₂O / methanol / 4 h / 50 °C

3.1: DIBAlH / toluene; hexane / 1.5 h / -78 °C

4.1: Ph₃P; diisopropylazodicarboxylate / diethyl ether / 0.33 h / -20 °C

4.2: diethyl ether / 12 h / -20 - 20 °C

4.3: 1.34 g / aq. TsOH / tetrahydrofuran / 4 h / 20 °C

5.1: 91 percent / Pd(OAc)2; Ag₂CO₃; diphenylphosphinopropane / 1,3-bis(diphenylphosphino)propane / toluene / 24 h / 107 °C

6.1: 91 percent / PPh₃ / CH₂Cl₂ / 0.17 h / 0 °C

7.1: 88 percent / Pd(PPh₃)4; Bu₃SnH / toluene / 0.33 h

8.1: 65 percent / Pd(OAc)2; Ag₂CO₃; diphenylphosphinopropane / 1,3-bis(diphenylphosphino)propane / toluene / 4 h / 107 °C

9.1: SeO₂; quartz sand / dioxane / 1.33 h / 75 °C

10.1: DIBALH / CH₂Cl₂; hexane; diethyl ether / -78 - 0 °C

10.2: NH₄Br / various solvents / 2 h / 20 °C

10.3: 89 percent / NaBH₄ / various solvents / 20 °C

11.1: LDA / tetrahydrofuran; hexane / -78 - 20 °C

11.2: 57 percent / tetrahydrofuran; hexane / 6 h / 20 °C / Irradiation

With palladium diacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; selenium(IV) oxide; di-isopropyl azodicarboxylate; [(ν³-allyl)PdCl]2; tri-n-butyl-tin hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; (+)-1(S),2(S)-bis<2'-(diphenylphosphino)benzamido>-1,2-diphenylethane; triethylamine; triphenylphosphine; diphenylphosphinopropane; silver carbonate; lithium diisopropyl amide; 1,3-bis-(diphenylphosphino)propane; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; dichloromethane; toluene; 4.2: Mitsunobu reaction / 5.1: Heck reaction;

DOI:10.1021/ja054449+

upstream raw materials:

methyl 6-hydroxy-cyclohex-1-enecarboxylate

2,2,2-Trichloroethyl chloroformate

Downstream raw materials:

(S)-(-)-methyl 6-(2-bromo-3-formyl-6-methoxyphenoxy)-cyclohex-1-enecarboxylate

2-<<(tert-butyldimethylsilyl)oxy>methyl>-1,3-cyclohexadiene

2-bromo-3-(2-hydroxymethyl-cyclohex-2-enyloxy)-4-methoxybenzylalcohol

2-bromo-1-(tert-butyldimethylsilyloxymethyl)-3-[2-(tertbutyldimethylsiloxymethyl)cyclohex-2-enyl-1-oxy]-4-methoxy-benzene