5-hydroxy-3-(phenylthio)butan-2-one ethylene acetal

Base Information

Chemical Name:5-hydroxy-3-(phenylthio)butan-2-one ethylene acetal
CAS No.:173310-61-7
Molecular Formula:C₁₃H₁₈O₃S
Molecular Weight:254.35
Hs Code.:

Synonyms:5-hydroxy-3-(phenylthio)butan-2-one ethylene acetal

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Chemical Property of 5-hydroxy-3-(phenylthio)butan-2-one ethylene acetal

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Technology Process of 5-hydroxy-3-(phenylthio)butan-2-one ethylene acetal

There total 2 articles about 5-hydroxy-3-(phenylthio)butan-2-one ethylene acetal 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: 87.0%

: 173310-59-3
methyl 4-oxo-3-(phenylthio)pentanoate ethylene acetal

: 173310-61-7
5-hydroxy-3-(phenylthio)butan-2-one ethylene acetal

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 0.5h;
DOI:10.1021/jo00131a013

Reference yield:

: 173310-57-1
4-oxo-3-(phenylthio)pentanoic acid methyl ester

: 173310-61-7
5-hydroxy-3-(phenylthio)butan-2-one ethylene acetal

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / p-TsOH / 24 h / Heating

2: 87 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

With lithium aluminium tetrahydride; toluene-4-sulfonic acid; In tetrahydrofuran;
DOI:10.1021/jo00131a013

Reference yield:

: 173310-61-7
5-hydroxy-3-(phenylthio)butan-2-one ethylene acetal

: (1R*,5R*,7S*)-4-(methoxycarbonyl)-1-methyl-7-(phenylthio)-8-oxabicyclo<3.2.1>octan-3-one

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) -78 deg C -> room temperature

2: 60 percent / aq. HCl / 24 h

3: TMSOTf / CH₂Cl₂ / 5 h / -78 °C

With hydrogenchloride; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; dimethyl sulfoxide; triethylamine; In dichloromethane;
DOI:10.1021/jo00131a013