1-[4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-3,5-dimethylphenyl]-5-hydroxy-1-pentanone

Base Information

• Chemical Name: 1-[4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-3,5-dimethylphenyl]-5-hydroxy-1-pentanone
• CAS No.: 144180-67-6
• Molecular Formula: C19H32O3Si
• Molecular Weight: 336.547
• DSSTox Substance ID: DTXSID701125997
• Mol file: 144180-67-6.mol

Synonyms:DTXSID701125997;1-[4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-3,5-dimethylphenyl]-5-hydroxy-1-pentanone;144180-67-6

Chemical Property of 1-[4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-3,5-dimethylphenyl]-5-hydroxy-1-pentanone

Chemical Property:

• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 336.21207141
• Heavy Atom Count: 23
• Complexity: 375

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC(=CC(=C1O[Si](C)(C)C(C)(C)C)C)C(=O)CCCCO

Technology Process of 1-[4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-3,5-dimethylphenyl]-5-hydroxy-1-pentanone

There total 1 articles about 1-[4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-3,5-dimethylphenyl]-5-hydroxy-1-pentanone 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:

3,4,5,6-tetrahydro-2H-pyran-2-one (542-28-9,26354-94-9) + 1-Bromo-4<(tert-butyldimethylsilyl)oxy>-3,5-dimethylbenzene (139229-99-5) → 1-<4-<(tert-butyldimethylsilyl)oxy>-3,5-dimethylphenyl>-5-hydroxy-1-pentanone (144180-67-6)

Guidance literature:

With tert.-butyl lithium; Yield given. Multistep reaction; 1.) pentane, ether, -78 deg C, 1 h, 2.) THF, -78 deg C, 1 h;

DOI:10.1021/jo00051a038

Reference yield: 88.0%

1-<4-<(tert-butyldimethylsilyl)oxy>-3,5-dimethylphenyl>-5-hydroxy-1-pentanone (144180-67-6) → 5-<4-<(tert-butyldimethylsilyl)oxy>-3,5-dimethylphenyl>pentanol (144180-69-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 12h; under 760 Torr;

DOI:10.1021/jo00051a038

Reference yield:

1-<4-<(tert-butyldimethylsilyl)oxy>-3,5-dimethylphenyl>-5-hydroxy-1-pentanone (144180-67-6) → (E)-7-<4-<(tert-butyldimethylsilyl)oxy>-3,5-dimethylphenyl>-2-heptenenitrile (144180-75-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / H₂ / 5percent Pd/C / ethanol / 12 h / 760 Torr

2: 1.) DMSO, oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, -50 deg C, 15 min, 2.) CH₂Cl₂, 0 deg C, 1 h

3: 1.) n-BuLi / 1.a) hexanes, ether, -78 deg C to r.t., b) r.t., 30 min, 2.a) ether, -78 deg C to r.t., b) r.t., overnight

With n-butyllithium; oxalyl dichloride; hydrogen; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In ethanol;

DOI:10.1021/jo00051a038

upstream raw materials:

3,4,5,6-tetrahydro-2H-pyran-2-one

1-Bromo-4<(tert-butyldimethylsilyl)oxy>-3,5-dimethylbenzene

Downstream raw materials:

5-<4-<(tert-butyldimethylsilyl)oxy>-3,5-dimethylphenyl>pentanol

5-(3,5-Dimethyl-4-oxo-cyclohexa-2,5-dienylidene)-pentanal

5-(3,5-dimethyl-4-hydroxyphenyl)pentanal

2,6-Dimethyl-4-(6-methyl-hept-5-enylidene)-cyclohexa-2,5-dienone