4-(1-benzyloxy-2-hydroxy)-3-trimethylsilylethynylpyridine

Base Information

Chemical Name:4-(1-benzyloxy-2-hydroxy)-3-trimethylsilylethynylpyridine
CAS No.:160540-47-6
Molecular Formula:C₁₉H₂₃NO₂Si
Molecular Weight:325.483
Hs Code.:

Synonyms:4-(1-benzyloxy-2-hydroxy)-3-trimethylsilylethynylpyridine

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Chemical Property of 4-(1-benzyloxy-2-hydroxy)-3-trimethylsilylethynylpyridine

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Technology Process of 4-(1-benzyloxy-2-hydroxy)-3-trimethylsilylethynylpyridine

There total 5 articles about 4-(1-benzyloxy-2-hydroxy)-3-trimethylsilylethynylpyridine 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%

: 4-(1-benzyloxy-2-tetrahydropyranyloxyethyl)-3-trimethylsilylethynylpyridine

: 160540-47-6
4-(1-benzyloxy-2-hydroxy)-3-trimethylsilylethynylpyridine

Guidance literature:: With toluene-4-sulfonic acid; In methanol; for 3h; Ambient temperature;
DOI:10.1016/S0040-4020(01)85672-6

Reference yield:

: 626-55-1,163928-56-1
3-Bromopyridine

: 160540-47-6
4-(1-benzyloxy-2-hydroxy)-3-trimethylsilylethynylpyridine

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) LDA / 1.) THF, hexane, -78 deg C, 15 min; 2.) THF, hexane, -78 deg C, 2 h

2: NaBH₄ / methanol / 0 - 25 °C

3: 1.) NaH / 1.) THF, r.t., 1 h; 2.) THF, r.t., overnight

4: 89 percent / Pd(PPh₃)4, Et₃N / 6 h / 100 °C / in sealed tube

5: 90 percent / p-TsOH*H₂O / methanol / 3 h / Ambient temperature

With sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydride; toluene-4-sulfonic acid; triethylamine; lithium diisopropyl amide; In methanol;
DOI:10.1016/S0040-4020(01)85672-6

Reference yield:

: 160540-44-3
3-bromo-4-(2-tetrahydropyranyloxyacetyl)pyridine

: 160540-47-6
4-(1-benzyloxy-2-hydroxy)-3-trimethylsilylethynylpyridine

Guidance literature:: Multi-step reaction with 4 steps

1: NaBH₄ / methanol / 0 - 25 °C

2: 1.) NaH / 1.) THF, r.t., 1 h; 2.) THF, r.t., overnight

3: 89 percent / Pd(PPh₃)4, Et₃N / 6 h / 100 °C / in sealed tube

4: 90 percent / p-TsOH*H₂O / methanol / 3 h / Ambient temperature

With sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydride; toluene-4-sulfonic acid; triethylamine; In methanol;
DOI:10.1016/S0040-4020(01)85672-6