(1R,2S,5R)-1-((E)-3-tert-Butoxy-propenyl)-2-isopropyl-5-methyl-cyclohexanol

Base Information

• Chemical Name: (1R,2S,5R)-1-((E)-3-tert-Butoxy-propenyl)-2-isopropyl-5-methyl-cyclohexanol
• CAS No.: 693833-31-7
• Molecular Formula: C₁₇H₃₂O₂
• Molecular Weight: 268.44

Synonyms:(1R,2S,5R)-1-((E)-3-tert-Butoxy-propenyl)-2-isopropyl-5-methyl-cyclohexanol

Chemical Property of (1R,2S,5R)-1-((E)-3-tert-Butoxy-propenyl)-2-isopropyl-5-methyl-cyclohexanol

Chemical Property:

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Technology Process of (1R,2S,5R)-1-((E)-3-tert-Butoxy-propenyl)-2-isopropyl-5-methyl-cyclohexanol

There total 1 articles about (1R,2S,5R)-1-((E)-3-tert-Butoxy-propenyl)-2-isopropyl-5-methyl-cyclohexanol 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: 70.0%

(2R,5S)-menthone (10458-14-7,14073-97-3,17627-49-5,7786-64-3) + 1(E)-Iodo-3-tert-butoxyprop-1-ene → (1R,2S,5R)-1-((E)-3-tert-Butoxy-propenyl)-2-isopropyl-5-methyl-cyclohexanol (693833-31-7)

Guidance literature:

1(E)-Iodo-3-tert-butoxyprop-1-ene; With tert.-butyl lithium; In diethyl ether; at -78 - 0 ℃; for 2.1h;

(2R,5S)-menthone; In diethyl ether; at -78 - 20 ℃; for 21h;

DOI:10.1139/v03-182

Reference yield:

(1R,2S,5R)-1-((E)-3-tert-Butoxy-propenyl)-2-isopropyl-5-methyl-cyclohexanol (693833-31-7) + methyl chloroformate (79-22-1) → Carbonic acid (1R,2S,5R)-1-((E)-3-tert-butoxy-propenyl)-2-isopropyl-5-methyl-cyclohexyl ester methyl ester

Guidance literature:

(1R,2S,5R)-1-((E)-3-tert-Butoxy-propenyl)-2-isopropyl-5-methyl-cyclohexanol; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 2h;

methyl chloroformate; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 4h;

DOI:10.1139/v03-182

Reference yield:

(1R,2S,5R)-1-((E)-3-tert-Butoxy-propenyl)-2-isopropyl-5-methyl-cyclohexanol (693833-31-7) → (1S,4R)-2-[(R)-3-tert-Butoxy-2-methyl-prop-(E)-ylidene]-1-isopropyl-4-methyl-cyclohexane

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 °C

1.2: tetrahydrofuran; hexane / 4 h / -78 - 0 °C

2.1: CuCN / tetrahydrofuran; diethyl ether / 1.5 h / -78 °C

2.2: 256 mg / tetrahydrofuran; diethyl ether / 17 h / -60 - 20 °C

With n-butyllithium; In tetrahydrofuran; diethyl ether; hexane;

DOI:10.1139/v03-182

upstream raw materials:

(2R,5S)-menthone

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