3-(S)-tetrahydropyranyloxy-4-(4-tetrahydropyranyloxy-3-methylphenyl)-1-butyne

Base Information

Chemical Name:3-(S)-tetrahydropyranyloxy-4-(4-tetrahydropyranyloxy-3-methylphenyl)-1-butyne
CAS No.:443147-26-0
Molecular Formula:C₂₁H₂₈O₄
Molecular Weight:344.451
Hs Code.:

Synonyms:3-(S)-tetrahydropyranyloxy-4-(4-tetrahydropyranyloxy-3-methylphenyl)-1-butyne

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Chemical Property of 3-(S)-tetrahydropyranyloxy-4-(4-tetrahydropyranyloxy-3-methylphenyl)-1-butyne

Chemical Property:

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Technology Process of 3-(S)-tetrahydropyranyloxy-4-(4-tetrahydropyranyloxy-3-methylphenyl)-1-butyne

There total 7 articles about 3-(S)-tetrahydropyranyloxy-4-(4-tetrahydropyranyloxy-3-methylphenyl)-1-butyne 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:

: 443147-34-0
1,1-dibromo-3-(S)-tetrahydropyranyloxy-4-(4-tetrahydropyranyloxy-3-methylphenyl)-1-butene

: 443147-26-0
3-(S)-tetrahydropyranyloxy-4-(4-tetrahydropyranyloxy-3-methylphenyl)-1-butyne

Guidance literature:: With n-butyllithium; In tetrahydrofuran; hexane; at -70 ℃;
DOI:10.1016/S0968-0896(02)00031-7

Reference yield:

: 148344-51-8
4-bromo-2-methyl-1-(2'-tetrahydropyranyloxy)benzene

: 443147-26-0
3-(S)-tetrahydropyranyloxy-4-(4-tetrahydropyranyloxy-3-methylphenyl)-1-butyne

Guidance literature:: Multi-step reaction with 8 steps

1.1: Mg; CuI / tetrahydrofuran / 0 °C

1.2: 100 percent / tetrahydrofuran

2.1: AcOH; H₂O / tetrahydrofuran / 65 °C

3.1: 2,4,6-collidine / CH₂Cl₂ / -78 °C

4.1: p-TsOH*H₂O / CH₂Cl₂ / 20 °C

5.1: 51 percent / 2N NaOH / methanol / 20 °C

6.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -70 - -30 °C

7.1: PPh₃; Et₃N / CH₂Cl₂ / -40 °C

8.1: n-BuLi / tetrahydrofuran; hexane / -70 °C

With 2,4,6-trimethyl-pyridine; sodium hydroxide; copper(l) iodide; n-butyllithium; oxalyl dichloride; water; toluene-4-sulfonic acid; magnesium; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1016/S0968-0896(02)00031-7

Reference yield:

: 2-(S)-hydroxy-3-(4-hydroxy-3-methylphenyl)propan-1-ol

: 443147-26-0
3-(S)-tetrahydropyranyloxy-4-(4-tetrahydropyranyloxy-3-methylphenyl)-1-butyne

Guidance literature:: Multi-step reaction with 6 steps

1: 2,4,6-collidine / CH₂Cl₂ / -78 °C

2: p-TsOH*H₂O / CH₂Cl₂ / 20 °C

3: 51 percent / 2N NaOH / methanol / 20 °C

4: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -70 - -30 °C

5: PPh₃; Et₃N / CH₂Cl₂ / -40 °C

6: n-BuLi / tetrahydrofuran; hexane / -70 °C

With 2,4,6-trimethyl-pyridine; sodium hydroxide; n-butyllithium; oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1016/S0968-0896(02)00031-7