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

Base Information

• Chemical Name: 5-Methyl-1-phenylsulfanyl-2,4,7,8-tetrahydro-3H-azulene-3a-carboxylic acid
• CAS No.: 76757-75-0
• Molecular Formula: C₁₈H₂₀O₂S
• Molecular Weight: 300.422

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

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

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

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

Reference yield:

N-(phenylthio)succinimide (14204-24-1) → 5-Methyl-1-phenylsulfanyl-2,4,7,8-tetrahydro-3H-azulene-3a-carboxylic acid (76757-75-0)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 90 percent / 10percent aq. NaOH / 20 h / Heating

With sodium hydroxide; lithium tetrafluoroborate; potassium hydride; In tetrahydrofuran;

DOI:10.1021/jo00322a017

Reference yield:

1-Phenylthiocyclopropyltriphenylphosphonium-tetrafluoroborat (58992-26-0) → 5-Methyl-1-phenylsulfanyl-2,4,7,8-tetrahydro-3H-azulene-3a-carboxylic acid (76757-75-0)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 90 percent / 10percent aq. NaOH / 20 h / Heating

With sodium hydroxide; potassium hydride;

DOI:10.1021/jo00322a017

upstream raw materials:

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

N-(phenylthio)succinimide

1-Phenylthiocyclopropyltriphenylphosphonium-tetrafluoroborat

Downstream raw materials:

(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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