3-(hydroxymethyl)cyclopentane

Base Information

• Chemical Name: 3-(hydroxymethyl)cyclopentane
• CAS No.: 113681-11-1
• Molecular Formula: C₆H₁₀O₂
• Molecular Weight: 114.144
• Hs Code.: 2914400090
• Mol file: 113681-11-1.mol

Synonyms:Cyclopentanone,3-(hydroxymethyl)-, (S)-

Chemical Property of 3-(hydroxymethyl)cyclopentane

Chemical Property:

• Boiling Point: 221.8±13.0 °C(Predicted)
• PKA: 14.71±0.10(Predicted)
• PSA: 37.30000
• Density: 1.099±0.06 g/cm3(Predicted)
• LogP: 0.34790
• Storage Temp.: 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

3-(hydroxymethyl)cyclopentanone 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3-(Hydroxymethyl)cyclopentanone is a reactant in the synthesis of D- and L-?Carbocyclic Nucleosides.

Technology Process of 3-(hydroxymethyl)cyclopentane

There total 19 articles about 3-(hydroxymethyl)cyclopentane 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: 100.0%

(3S)-3-(tert-butyldimethylsilyloxy)methylcyclopentan-1-one → (S)-3-(hydroxymethyl)-1-cyclopentanone (113681-11-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1021/ja970901g

Reference yield: 82.0%

(S)-3-(((tert-butyldiphenylsilyl)oxy)methyl)cyclopentanone (1071906-18-7) → (S)-3-(hydroxymethyl)-1-cyclopentanone (113681-11-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1021/ol801791g

Reference yield:

4(R)-(((tert-butyldimethylsilyl)oxy)methyl)-2-cyclopentenone (196303-34-1) → (S)-3-(hydroxymethyl)-1-cyclopentanone (113681-11-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / H₂ / Pd on C / CH₂Cl₂ / 6 h / 25 °C / 760 Torr

2: 100 percent / tetrabutylammonium fluoride monohydrate / tetrahydrofuran / 1 h / 0 °C

With tetrabutyl ammonium fluoride; hydrogen; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; 1: Hydrogenation / 2: desilylation;

DOI:10.1021/ja970901g

upstream raw materials:

[(ethoxymethoxy)methyl]benzene

tri-n-butylstannylmethanol

(+)-(R)-2-(p-tolylsulfinyl)cyclopent-2-enone

(2R,3R,R_S)-3-(hydroxymethyl)-2-[(2,4,6-trimethylphenyl)sulfinyl]-1-cyclopentanone

Refernces

• 1、 Marce, Patricia,Diaz, Yolanda,Matheu, M. Isabel,Castillon, Sergio. "Synthesis of D- And L-carbocyclic nucleosides via rhodium-catalyzed asymmetric hydroacylation as the key step". supporting information; experimental part. p. 4735 - 4738. Retrieved 2009/05/31.
• 2、 Fonquerna,Moyana,Pericas,Riera. "Totally stereocontrolled intermolecular Pauson-Khand reactions of N-(2-alkynoyl) sultams". . p. 10225 - 10226. Retrieved 2007/10/03.