2-Hydroxymethyl-2-cyclopentenoneethyleneketal

Base Information

• Chemical Name: 2-Hydroxymethyl-2-cyclopentenoneethyleneketal
• CAS No.: 80963-19-5
• Molecular Formula: C8H12O3
• Molecular Weight: 156.17908
• Mol file: 80963-19-5.mol

Synonyms:2-hydroxymethyl-2-cyclopentenone ethylene ketal;2-Hydroxymethyl-2-cyclopentenoneethyleneketal;

Chemical Property of 2-Hydroxymethyl-2-cyclopentenoneethyleneketal

Chemical Property:

• PSA: 38.69000
• LogP: 0.44200

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Hydroxymethyl-2-cyclopentenoneethyleneketal

There total 5 articles about 2-Hydroxymethyl-2-cyclopentenoneethyleneketal 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:

6-carbethoxy-1,4-dioxaspiro<4.4>non-6-ene (80963-24-2) → α-(hydroxymethyl)cyclopentenone ethylene ketal (80963-19-5)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -78 ℃; for 7h;

DOI:10.1021/jo00349a009

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 6-bromo-1,4-dioxa-spiro[4.4]non-6-ene (68241-78-1) → α-(hydroxymethyl)cyclopentenone ethylene ketal (80963-19-5)

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction; 1.) THF, -78 deg C, 60 min, 2.) -78 deg C;

DOI:10.1021/jo00349a009

Reference yield:

6-bromo-1,4-dioxa-spiro[4.4]non-6-ene (68241-78-1) → α-(hydroxymethyl)cyclopentenone ethylene ketal (80963-19-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) n-BuLi, 2.) / 1.) THF, -78 deg C, 2.) -78 deg C

2: DIBAL / toluene / 7 h / -78 °C

With n-butyllithium; diisobutylaluminium hydride; In toluene;

DOI:10.1021/jo00349a009

upstream raw materials:

formaldehyd

6-bromo-1,4-dioxa-spiro[4.4]non-6-ene

6-carbethoxy-1,4-dioxaspiro<4.4>non-6-ene

2-bromo-2-cyclopenten-1-one

Downstream raw materials:

(+/-)-Homosarkomycin

(5-oxocyclopent-1-en-1-yl)methyl acetate

(+/-)-epipentenomycin I

(+/-)-pentenomycin II

Refernces

• 1、 Smith III,Branca,Pilla,Guaciaro. "Stereocontrolled total synthesis of (±)-pentenomycins I-III, their epimers, and dehydropentenomycin I". . p. 1855 - 1869. Retrieved 2007/10/02.