trans-1-(4-chlorobenzylthio)-4-[(1E,3E)-4-[4-(trifluoromethyl)phenyl]-1,3-butadienyl]cyclohexane

Base Information

• Chemical Name: trans-1-(4-chlorobenzylthio)-4-[(1E,3E)-4-[4-(trifluoromethyl)phenyl]-1,3-butadienyl]cyclohexane
• CAS No.: 183801-09-4
• Molecular Formula: C₂₄H₂₄ClF₃S
• Molecular Weight: 436.969

Synonyms:trans-1-(4-chlorobenzylthio)-4-[(1E,3E)-4-[4-(trifluoromethyl)phenyl]-1,3-butadienyl]cyclohexane

Chemical Property of trans-1-(4-chlorobenzylthio)-4-[(1E,3E)-4-[4-(trifluoromethyl)phenyl]-1,3-butadienyl]cyclohexane

Chemical Property:

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Technology Process of trans-1-(4-chlorobenzylthio)-4-[(1E,3E)-4-[4-(trifluoromethyl)phenyl]-1,3-butadienyl]cyclohexane

There total 6 articles about trans-1-(4-chlorobenzylthio)-4-[(1E,3E)-4-[4-(trifluoromethyl)phenyl]-1,3-butadienyl]cyclohexane 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: 31.0%

trans-4-(4-chlorobenzylthio)cyclohexanecarbaldehyde (183801-07-2) + [(E)-(p-(trifluoromethyl)cinnamyl)triphenylphosphonium] chloride → trans-1-(4-chlorobenzylthio)-4-[(1E,3E)-4-[4-(trifluoromethyl)phenyl]-1,3-butadienyl]cyclohexane (183801-09-4)

Guidance literature:

[(E)-(p-(trifluoromethyl)cinnamyl)triphenylphosphonium] chloride; With dimsylsodium; In dimethyl sulfoxide; at 55 ℃; for 2.5h;

trans-4-(4-chlorobenzylthio)cyclohexanecarbaldehyde; In dimethyl sulfoxide; at 20 ℃; for 0.25h;

DOI:10.1248/cpb.48.694

Reference yield:

(4-chlorophenyl)methanethiol (6258-66-8) → trans-1-(4-chlorobenzylthio)-4-[(1E,3E)-4-[4-(trifluoromethyl)phenyl]-1,3-butadienyl]cyclohexane (183801-09-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaH / dimethylformamide / 0.08 h / 0 °C

1.2: 68 percent / dimethylformamide / 1 h / 50 °C

2.1: 100 percent / 2 M aq. HCl / acetone / 2 h / 50 °C

3.1: NaCH₂SOMe / dimethylsulfoxide / 20 °C

3.2: 78 percent / dimethylsulfoxide / 20 °C

4.1: 5 M aq. HCl / acetone / 2 h / 55 °C

4.2: 24 percent / NaOMe / methanol / 2 h / 20 °C

5.1: NaCH₂SOMe / dimethylsulfoxide / 2.5 h / 55 °C

5.2: 31 percent / dimethylsulfoxide / 0.25 h / 20 °C

With hydrogenchloride; dimsylsodium; sodium hydride; In dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; 1.1: Metallation / 1.2: Condensation / 2.1: Hydrolysis / 3.1: Metallation / 3.2: Condensation / 4.1: acidolysis / 4.2: epimerization / 5.1: Metallation / 5.2: Condensation;

DOI:10.1248/cpb.48.694

Reference yield:

8-methylsulfonyloxy-1,4-dioxaspiro[4.5]decane (141120-33-4) → trans-1-(4-chlorobenzylthio)-4-[(1E,3E)-4-[4-(trifluoromethyl)phenyl]-1,3-butadienyl]cyclohexane (183801-09-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaH / dimethylformamide / 0.08 h / 0 °C

1.2: 68 percent / dimethylformamide / 1 h / 50 °C

2.1: 100 percent / 2 M aq. HCl / acetone / 2 h / 50 °C

3.1: NaCH₂SOMe / dimethylsulfoxide / 20 °C

3.2: 78 percent / dimethylsulfoxide / 20 °C

4.1: 5 M aq. HCl / acetone / 2 h / 55 °C

4.2: 24 percent / NaOMe / methanol / 2 h / 20 °C

5.1: NaCH₂SOMe / dimethylsulfoxide / 2.5 h / 55 °C

5.2: 31 percent / dimethylsulfoxide / 0.25 h / 20 °C

With hydrogenchloride; dimsylsodium; sodium hydride; In dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; 1.1: Metallation / 1.2: Condensation / 2.1: Hydrolysis / 3.1: Metallation / 3.2: Condensation / 4.1: acidolysis / 4.2: epimerization / 5.1: Metallation / 5.2: Condensation;

DOI:10.1248/cpb.48.694

upstream raw materials:

trans-4-(4-chlorobenzylthio)cyclohexanecarbaldehyde

(4-chlorophenyl)methanethiol

8-methylsulfonyloxy-1,4-dioxaspiro[4.5]decane

4-(4-chlorobenzylthio)cyclohexanone

Downstream raw materials:

S-[trans-4-[(1E,3E)-4-[4-(trifluoromethyl)phenyl]-1,3-butadienyl]cyclohexyl] thioacetate

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