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

Base Information

• Chemical Name: 2H-Cyclopenta[b]furan-2-one, 3,3a,4,6a-tetrahydro-3-(hydroxymethylene)-, [3aS-(3Z,3aalpha,6aalpha)]- (9CI)
• CAS No.: 194468-85-4
• Molecular Formula: C8H8 O3
• Molecular Weight: 152.14732
• Mol file: 194468-85-4.mol

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

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

Chemical Property:

• PSA: 46.53000
• LogP: 0.92980

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)-, [3aS-(3Z,3aalpha,6aalpha)]- (9CI)

There total 2 articles about 2H-Cyclopenta[b]furan-2-one, 3,3a,4,6a-tetrahydro-3-(hydroxymethylene)-, [3aS-(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: 96.0%

p-toluenesulfonyl chloride (98-59-9) + (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) → Toluene-4-sulfonic acid (3aS,6aS)-2-oxo-4,6a-dihydro-3aH-cyclopenta[b]furan-(3E)-ylidenemethyl ester (194468-86-5)

Guidance literature:

With triethylamine; In dichloromethane; at -30 ℃; for 1h;

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

upstream raw materials:

(3aS,6aR)-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one

formic acid ethyl ester

(3aS,6R,6aR)-6-iodohexahydro-2H-cyclopenta[b]furan-2-one

Downstream raw materials:

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

Toluene-4-sulfonic acid (3aS,6aS)-2-oxo-4,6a-dihydro-3aH-cyclopenta[b]furan-(3E)-ylidenemethyl ester

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