2H-Cyclopenta[b]furan-2-one, 3,3a,4,6a-tetrahydro-3-(hydroxymethylene)-, (3Z,3aalpha,6aalpha)- (9CI)

Base Information

• Chemical Name: 2H-Cyclopenta[b]furan-2-one, 3,3a,4,6a-tetrahydro-3-(hydroxymethylene)-, (3Z,3aalpha,6aalpha)- (9CI)
• CAS No.: 205815-42-5
• Molecular Formula: C₈H₈O₃
• Molecular Weight: 152.15
• Mol file: 205815-42-5.mol

Synonyms:2H-Cyclopenta[b]furan-2-one,3,3a,4,6a-tetrahydro-3-(hydroxymethylene)-, (3Z,3aa,6aa)- (9CI)

Chemical Property of 2H-Cyclopenta[b]furan-2-one, 3,3a,4,6a-tetrahydro-3-(hydroxymethylene)-, (3Z,3aalpha,6aalpha)- (9CI)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2H-Cyclopenta[b]furan-2-one, 3,3a,4,6a-tetrahydro-3-(hydroxymethylene)-, (3Z,3aalpha,6aalpha)- (9CI)

There total 5 articles about 2H-Cyclopenta[b]furan-2-one, 3,3a,4,6a-tetrahydro-3-(hydroxymethylene)-, (3Z,3aalpha,6aalpha)- (9CI) 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: 78.0%

(3aS,6aR)-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one (56487-70-8) + formic acid ethyl ester (109-94-4) → (3aS,6aS)-3-[1-Hydroxy-meth-(Z)-ylidene]-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one (194468-85-4,205673-22-9,205815-42-5)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 23 ℃; for 20h;

DOI:10.1016/S0040-4020(98)00077-5

Reference yield:

(3aS,6R,6aR)-6-iodohexahydro-2H-cyclopenta[b]furan-2-one (160080-50-2) → (3aS,6aS)-3-[1-Hydroxy-meth-(Z)-ylidene]-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one (194468-85-4,205673-22-9,205815-42-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / DBU / tetrahydrofuran / 1.) 50 deg C, 2 h, 2.) 70 deg C, 90 min

2: 78 percent / NaH / tetrahydrofuran / 20 h / 23 °C

With sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran;

DOI:10.1016/S0040-4020(98)00077-5

Reference yield:

(cyclopent-2-eneyl)acetic acid (13668-61-6) → 3-[1-Hydroxy-meth-(E)-ylidene]-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one (78646-68-1,205815-42-5)

Guidance literature:

Multi-step reaction with 3 steps

1: hypoiodous acid

2: 1,5-diazabicyclo<5.4.0>undec-5-ene / tetrahydrofuran / 1.) 50 deg C, 2 h, 2.) reflux, 90 min

3: NaOEt

With hypoiodous acid; sodium ethanolate; 1,5-Diazabicyclo[5.4.0]undec-5-ene; In tetrahydrofuran;

DOI:10.1039/P19810001734

upstream raw materials:

3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one

formic acid ethyl ester

(cyclopent-2-eneyl)acetic acid

6-iodo-3,3a,4,5,6,6a-hexahydrocyclopentafuran-2-one

Downstream raw materials:

(3aR,6aR)-3-[1-((2R,3R,4S)-4-Methyl-5-oxo-3-phenylsulfanyl-tetrahydro-furan-2-yloxy)-meth-(E)-ylidene]-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one