5,5-Ethylenedioxy-3-hydroxy-4,4-tetramethylene-1-phenylthio-1-hexyne

Base Information

• Chemical Name: 5,5-Ethylenedioxy-3-hydroxy-4,4-tetramethylene-1-phenylthio-1-hexyne
• CAS No.: 317350-57-5
• Molecular Formula: C₁₈H₂₂O₃S
• Molecular Weight: 318.437
• Mol file: 317350-57-5.mol

Synonyms:5,5-Ethylenedioxy-3-hydroxy-4,4-tetramethylene-1-phenylthio-1-hexyne

Chemical Property of 5,5-Ethylenedioxy-3-hydroxy-4,4-tetramethylene-1-phenylthio-1-hexyne

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5,5-Ethylenedioxy-3-hydroxy-4,4-tetramethylene-1-phenylthio-1-hexyne

There total 1 articles about 5,5-Ethylenedioxy-3-hydroxy-4,4-tetramethylene-1-phenylthio-1-hexyne 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: 81.0%

phenylthioacetylene (6228-98-4) + 1-(2-Methyl-[1,3]dioxolan-2-yl)-cyclopentanecarbaldehyde (137709-52-5) → 5,5-Ethylenedioxy-3-hydroxy-4,4-tetramethylene-1-phenylthio-1-hexyne (317350-57-5)

Guidance literature:

phenylthioacetylene; With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; In tetrahydrofuran; hexane; at -50 ℃; for 0.5h;

1-(2-Methyl-[1,3]dioxolan-2-yl)-cyclopentanecarbaldehyde; In tetrahydrofuran; hexane; at -50 ℃; for 0.666667h; Further stages.;

DOI:10.1002/1521-3765(20001103)6:21<3897::AID-CHEM3897>3.0.CO;2-1

Reference yield: 98.0%

5,5-Ethylenedioxy-3-hydroxy-4,4-tetramethylene-1-phenylthio-1-hexyne (317350-57-5) → 3-Hydroxy-4,4-tetramethylene-1-phenylthio-1-hexyn-5-one (317350-58-6)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; at 20 ℃; for 1h;

DOI:10.1002/1521-3765(20001103)6:21<3897::AID-CHEM3897>3.0.CO;2-1

Reference yield:

5,5-Ethylenedioxy-3-hydroxy-4,4-tetramethylene-1-phenylthio-1-hexyne (317350-57-5) → 4,5-[Di(tert-butyl)silylenedioxy]-7,8-dimethoxy-2,2-tetramethylene-9-phenylsulfinyl-2,3-dihydrobenz[f]indene-1,3-dione (317350-30-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / p-TsOH*H₂O / acetone / 1 h / 20 °C

2: 100 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 20 °C

3: 88 percent / LiN(TMS)2 / tetrahydrofuran / 0.5 h / -78 °C

4: 64 percent / DMSO; PCC; pyridinium trifluoroacetate / benzene / 1 h / 20 °C

5: 57 percent

6: 78 percent / mCPBA / CH₂Cl₂ / 0.5 h / -40 °C

With dmap; pyridinium trifluroacetate; toluene-4-sulfonic acid; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; acetone; benzene;

DOI:10.1002/1521-3765(20001103)6:21<3897::AID-CHEM3897>3.0.CO;2-1

upstream raw materials:

phenylthioacetylene

1-(2-Methyl-[1,3]dioxolan-2-yl)-cyclopentanecarbaldehyde

Downstream raw materials:

3-Hydroxy-4,4-tetramethylene-1-phenylthio-1-hexyn-5-one

4,4-Tetramethylene-5-oxo-1-phenylthio-1-hexyn-3-yl 2-benzyloxy-4,5-dimethoxy benzoate

1-(2-Benzyloxy-4,5-dimethoxyphenyl)-5-hydroxy-4,4-tetramethylene-7-phenylthio-6-heptyne-1,3-dione

1-(2-Benzyloxy-4,5-dimethoxyphenyl)-4,4-tetramethylene-7-phenylthio-6-heptyne-1,3,5-trione