5-Methyl-1-phenylsulfanyl-2,4,7,8-tetrahydro-3H-azulene-3a-carboxylic acid methyl ester

Base Information

• Chemical Name: 5-Methyl-1-phenylsulfanyl-2,4,7,8-tetrahydro-3H-azulene-3a-carboxylic acid methyl ester
• CAS No.: 76773-01-8
• Molecular Formula: C₁₉H₂₂O₂S
• Molecular Weight: 314.448

Synonyms:5-Methyl-1-phenylsulfanyl-2,4,7,8-tetrahydro-3H-azulene-3a-carboxylic acid methyl ester

Chemical Property of 5-Methyl-1-phenylsulfanyl-2,4,7,8-tetrahydro-3H-azulene-3a-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of 5-Methyl-1-phenylsulfanyl-2,4,7,8-tetrahydro-3H-azulene-3a-carboxylic acid methyl ester

There total 2 articles about 5-Methyl-1-phenylsulfanyl-2,4,7,8-tetrahydro-3H-azulene-3a-carboxylic acid methyl 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:

N-(phenylthio)succinimide (14204-24-1) → 5-Methyl-1-phenylsulfanyl-2,4,7,8-tetrahydro-3H-azulene-3a-carboxylic acid methyl ester (76773-01-8)

Guidance literature:

Multi-step reaction with 2 steps

1: LiBF₄ / tetrahydrofuran / 1 h / -30 °C

2: 1.) KH / 1.) THF, room temp., 10 min, 2.) reflux, 3 d

With lithium tetrafluoroborate; potassium hydride; In tetrahydrofuran;

DOI:10.1021/jo00322a017

Reference yield:

1-Phenylthiocyclopropyltriphenylphosphonium-tetrafluoroborat (58992-26-0) + 2-(carbomethoxy)-4-methylcyclohept-4-en-1-one (76757-71-6) → 5-Methyl-1-phenylsulfanyl-2,4,7,8-tetrahydro-3H-azulene-3a-carboxylic acid methyl ester (76773-01-8)

Guidance literature:

With potassium hydride; Yield given. Multistep reaction; 1.) THF, room temp., 10 min, 2.) reflux, 3 d;

DOI:10.1021/jo00322a017

Reference yield: 90.0%

5-Methyl-1-phenylsulfanyl-2,4,7,8-tetrahydro-3H-azulene-3a-carboxylic acid methyl ester (76773-01-8) → 5-Methyl-1-phenylsulfanyl-2,4,7,8-tetrahydro-3H-azulene-3a-carboxylic acid (76757-75-0)

Guidance literature:

With sodium hydroxide; for 20h; Heating;

DOI:10.1021/jo00322a017

upstream raw materials:

1-Phenylthiocyclopropyltriphenylphosphonium-tetrafluoroborat

2-(carbomethoxy)-4-methylcyclohept-4-en-1-one

N-(phenylthio)succinimide

Downstream raw materials:

5-Methyl-1-phenylsulfanyl-2,4,7,8-tetrahydro-3H-azulene-3a-carboxylic acid

(1S,8R,9R)-8-Iodo-9-methyl-4-phenylsulfanyl-10-oxa-tricyclo[7.2.1.0^1,5]dodec-4-en-11-one

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