1-({[(1S,2S)-2-ethenylcyclopropyl]methoxy}methyl)-4-methoxybenzene

Base Information

• Chemical Name: 1-({[(1S,2S)-2-ethenylcyclopropyl]methoxy}methyl)-4-methoxybenzene
• CAS No.: 1314079-44-1
• Molecular Formula: C₁₄H₁₈O₂
• Molecular Weight: 218.296
• Mol file: 1314079-44-1.mol

Synonyms:1-({[(1S,2S)-2-ethenylcyclopropyl]methoxy}methyl)-4-methoxybenzene

Chemical Property of 1-({[(1S,2S)-2-ethenylcyclopropyl]methoxy}methyl)-4-methoxybenzene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-({[(1S,2S)-2-ethenylcyclopropyl]methoxy}methyl)-4-methoxybenzene

There total 9 articles about 1-({[(1S,2S)-2-ethenylcyclopropyl]methoxy}methyl)-4-methoxybenzene 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: 91.0%

1-({[(1S,2R)-2-Ethynylcyclopropyl]methoxy}methyl)-4-methoxybenzene → 1-({[(1S,2S)-2-ethenylcyclopropyl]methoxy}methyl)-4-methoxybenzene (1314079-44-1)

Guidance literature:

With Schwartz's reagent; In dichloromethane; at 23 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.joc.8b02137

Reference yield: 74.0%

(1R,2S)-2-{[(4-methoxybenzyl)oxy]methyl}cyclopropanecarbaldehyde (617705-29-0) → 1-({[(1S,2S)-2-ethenylcyclopropyl]methoxy}methyl)-4-methoxybenzene (1314079-44-1)

Guidance literature:

methyltriphenylphosphonium halide; With sodium hexamethyldisilazane; In tetrahydrofuran; at 20 ℃; for 0.5h;

(1R,2S)-2-{[(4-methoxybenzyl)oxy]methyl}cyclopropanecarbaldehyde; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1021/ol2015994

Reference yield:

[(1S,2R)-2-[2-(triisopropylsilyl)ethynyl]cyclopropyl]methanol → 1-({[(1S,2S)-2-ethenylcyclopropyl]methoxy}methyl)-4-methoxybenzene (1314079-44-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: Dess-Martin periodane / dichloromethane / 1 h / Inert atmosphere

2.1: sodium dihydrogenphosphate; 2-methyl-but-2-ene; sodium chlorite; water / tetrahydrofuran / 0.25 h / 23 °C

3.1: dmap / dichloromethane / 0.17 h / 23 °C / Inert atmosphere

3.2: 16.5 h / 23 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / diethyl ether; hexane / 3 h / 23 °C / Inert atmosphere

5.1: toluene-4-sulfonic acid / dichloromethane / 24 h / 23 °C / Inert atmosphere

6.1: methanol; silver fluoride / 3 h / 23 °C / Inert atmosphere

7.1: Schwartz's reagent / dichloromethane / 2 h / 23 °C / Inert atmosphere

With methanol; dmap; sodium chlorite; sodium dihydrogenphosphate; Schwartz's reagent; 2-methyl-but-2-ene; water; silver fluoride; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;

DOI:10.1021/acs.joc.8b02137

upstream raw materials:

(1R,2S)-2-{[(4-methoxybenzyl)oxy]methyl}cyclopropanecarbaldehyde

O-(4-methoxybenzyl)-trichloroacetimidate

Downstream raw materials:

methyl (3R,4E)-3-hydroxy-5-[(1S,2S)-2-(((4-methoxyphenyl)methoxy)methyl)cyclopropyl]pent-4-enoate