22929-52-8

Usage

Chemical Properties

Colorless transparent liquid

InChI:InChI=1/C4H6O2/c5-4-1-2-6-3-4/h1-3H2

Synthetic route

3-Hydroxytetrahydrofuran (453-20-3) → tetrahydrofuran-3-one (22929-52-8)

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid In dichloromethane at -5 - 20℃; for 1h; Solvent;	95%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid In dichloromethane at -5 - 20℃; for 1h; Solvent;	95%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid In dichloromethane at -5 - 20℃; for 1h; Solvent;	95%

methyl 4-oxotetrahydrofuran-3-carboxylate (57595-23-0) → tetrahydrofuran-3-one (22929-52-8)

Conditions	Yield
With sulfuric acid at 100℃; for 3h; Reagent/catalyst; Temperature;	90.7%
In sulfuric acid	6.8 g (79%)

ethyl tetrahydrofuran-3-one 4-carboxylate (89898-51-1) → tetrahydrofuran-3-one (22929-52-8)

Conditions	Yield
With sulfuric acid at 80℃; for 5h; Reagent/catalyst;	82.3%

2,3-dihydro-2H-furan (1191-99-7) → tetrahydrofuran-3-one (22929-52-8) + RS(SR)-2,3-dibromotetrahydrofuran (20245-14-1, 52911-58-7, 138610-15-8) + trans-3-bromo-2-hydroxytetrahydrofuran

Conditions	Yield
With water; oxygen; lithium bromide; copper(ll) bromide In tetrahydrofuran at 25℃; under 760.051 Torr;	A 15% B 75% C 10%

3-hydroxyfuran (29212-66-6) → tetrahydrofuran-3-one (22929-52-8)

Conditions	Yield
Stage #1: 3-hydroxyfuran With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide In dichloromethane; water ice-water bath; Stage #2: With sodium hypochlorite; sodium hydrogencarbonate In dichloromethane; water at 0 - 5℃; for 2.66667h;	67%
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide In dichloromethane at 0 - 5℃; for 2.66667h; pH=9.5;	67%
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0 - 5℃; for 2.66667h; pH=9.5;	67%

(+-)-tetrahydro-furan-3-ol → tetrahydrofuran-3-one (22929-52-8)

Conditions	Yield
With copper oxide-chromium oxide catalyst at 200 - 250℃;
With sodium dichromate; diethyl ether; sulfuric acid

2,3-dihydro-2H-furan (1191-99-7) → tetrahydrofuran-3-one (22929-52-8) + (2S,3S)-3-chlorotetrahydrofuran-2-ol (1120-74-7, 29120-51-2, 29307-02-6) + (2R,3R)-3-chlorotetrahydrofuran-2-ol + 2-chloro-3-hydroxytetrahydrofuran

Conditions	Yield
With (R)-2,2'-bis[bis(3-methylphenyl)phosphino]-1,1'-binaphthyl; copper dichloride; palladium (II) ion Title compound not separated from byproducts;

2,5-dihydrofuran (1708-29-8) → tetrahydrofuran-3-one (22929-52-8)

Conditions	Yield
With dinitrogen monoxide In benzene at 220℃; for 12h; pressure;

1-butyn-4-ol (927-74-2) → tetrahydrofuran-3-one (22929-52-8)

Conditions	Yield
With 5-bromo-2-methyl-pyridine-N-oxide; [BrettPhosAu]NTf2; trifluoroacetic acid In 1,2-dichloro-ethane at 20℃; for 6h; Inert atmosphere; Darkness;	42 %Spectr.

tetrahydrofuran-3-one (22929-52-8) + 4-methoxybenzenesulfonyl hydrazide (1950-68-1) → N'-(dihydrofuran-3(2H)-ylidene)-4-methoxybenzene-sulfonohydrazide (1510865-64-1)

Conditions	Yield
In methanol at 20℃; Schlenk technique;	100%

tetrahydrofuran-3-one (22929-52-8) + toluene-4-sulfonic acid hydrazide (1576-35-8) → N'-(dihydrofuran-3(2H)-ylidene)-4-methylbenzene-sulfonohydrazide (1708-19-6)

Conditions	Yield
In methanol at 20℃; Schlenk technique;	100%

tetrahydrofuran-3-one (22929-52-8) + C26H37FN4O4 → C30H43FN4O5

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; for 0.75h;	99%
Stage #1: tetrahydrofuran-3-one; C26H37FN4O4 With acetic acid In dichloromethane at 20℃; for 0.75h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃;

tetrahydrofuran-3-one (22929-52-8) + acetylenemagnesium bromide (4301-14-8) → 1-ethynyl-3-oxacyclopentanol (137344-86-6)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 0.5h; Inert atmosphere;	97%
Stage #1: tetrahydrofuran-3-one; acetylenemagnesium bromide In tetrahydrofuran at 0 - 20℃; Stage #2: With water; ammonium chloride In tetrahydrofuran	57%

tetrahydrofuran-3-one (22929-52-8) + nitromethane (75-52-5) → 3‑nitromethylidenetetrahydrofuran

Conditions	Yield
With sodium methylate In methanol at 20 - 30℃; for 6h; Reagent/catalyst; Temperature;	96.7%

tetrahydrofuran-3-one (22929-52-8) + sodium cyanide (773837-37-9) → 3-aminotetrahydrofuran-3-carbonitrile hydrochloride

Conditions	Yield
Stage #1: tetrahydrofuran-3-one With ammonia; acetic acid In methanol at 20℃; for 0.166667h; Cooling with ice; Stage #2: sodium cyanide In methanol at 20 - 50℃; for 2h; Stage #3: With hydrogenchloride In 1,4-dioxane; dichloromethane at 20℃; for 0.25h;	96%

tetrahydrofuran-3-one (22929-52-8) + tert-Butoxybis(dimethylamino)methane (5815-08-7) → (E)-4-((dimethylamino)methylene)dihydrofuran-3(2H)-one

Conditions	Yield
In toluene at 20℃; for 18h;	90%

tetrahydrofuran-3-one (22929-52-8) + trimethylsilylacetylene (1066-54-2) → 3-((trimethylsilyl)ethynyl)tetrahydrofuran-3-ol

Conditions	Yield
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: tetrahydrofuran-3-one In tetrahydrofuran at -78 - 20℃; for 1.33333h;	89%
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: tetrahydrofuran-3-one In tetrahydrofuran at -78 - 20℃; for 1.33333h; Inert atmosphere;	89%

tetrahydrofuran-3-one (22929-52-8) + phenylacetylene (536-74-3) → 3-(phenylethynyl)tetrahydrofuran-3-ol

Conditions	Yield
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: tetrahydrofuran-3-one In tetrahydrofuran; hexane at -78 - 20℃; for 2h;	89%

tetrahydrofuran-3-one (22929-52-8) + N,N-dimethylammonium chloride (506-59-2) + potassium cyanide (151-50-8) → 3-cyano-3-dimethylamino-tetrahydrofurane (176445-75-3)

Conditions	Yield
In water Ambient temperature;	88%

tetrahydrofuran-3-one (22929-52-8) + ethyl 1-(6-(3,5-difluoro-2-((2-methyl-4-(piperidin-4-yl)benzyl)oxy)phenyl)pyridin-2-yl)piperidine-4-carboxylate → ethyl 1-(6-(3,5-difluoro-2-((2-methyl-4-(1-(tetrahydrofuran-3-yl)piperidin-4-yl)benzyl)oxy)phenyl)pyridin-2-yl)piperidine-4-carboxylate

Conditions	Yield
Stage #1: tetrahydrofuran-3-one; ethyl 1-(6-(3,5-difluoro-2-((2-methyl-4-(piperidin-4-yl)benzyl)oxy)phenyl)pyridin-2-yl)piperidine-4-carboxylate In methanol at 25℃; for 3h; Molecular sieve; Stage #2: With sodium cyanoborohydride In methanol at 50℃; for 12h;	88%

tetrahydrofuran-3-one (22929-52-8) + 1,1,1,3,3,3-hexafluoropropan-2-yl 1-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carbonyl)-1,8-diazaspiro[4.5]decane-8-carboxylate → 1,1,1,3,3,3-hexafluoropropan-2-yl 1-(7-(tetrahydrofuran-3-yl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carbonyl)-1,8-diazaspiro[4.5]decane-8-carboxylate

Conditions	Yield
Stage #1: tetrahydrofuran-3-one; 1,1,1,3,3,3-hexafluoropropan-2-yl 1-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carbonyl)-1,8-diazaspiro[4.5]decane-8-carboxylate With triethylamine In 1,2-dichloro-ethane at 20℃; for 1.5h; Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 4h;	86%

tetrahydrofuran-3-one (22929-52-8) + nitromethane (75-52-5) → C5H9NO4

Conditions	Yield
With triethylamine In ethanol at 20℃; for 18h;	85.9%

tetrahydrofuran-3-one (22929-52-8) + methanesulfonic acid (75-75-2) + homoalylic alcohol (627-27-0) → methanesulfonic acid 2,6-dioxaspiro[4.5]dec-9-yl ester (503551-88-0)

Conditions	Yield
In dichloromethane at 23℃; Prins cyclization;	85%
In dichloromethane at 25℃; for 16h;

tetrahydrofuran-3-one (22929-52-8) + trans-3-((2-methyl-6-(5-methyl-6-(piperidin-4-yl)-1H-indazol-1-yl)pyrimidin-4-yl)amino)cyclobutanol → trans-3-((2-methyl-6-(5-methyl-6-(1-(tetrahydrofuran-3-yl)piperidin-4-yl)-1H-indazol-1-yl)pyrimidin-4-yl)amino)cyclobutanol

Conditions	Yield
With sodium cyanoborohydride; acetic acid In 1,2-dichloro-ethane at 20℃; for 6h;	85%

tetrahydrofuran-3-one (22929-52-8) + isoquinoline (119-65-3) → 1-(4-oxotetrahydrofuran-2-yl)isoquinoline

Conditions	Yield
With sodium persulfate; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; trifluoroacetic acid In water at 23℃; for 24h; Minisci Aromatic Substitution; Inert atmosphere; Irradiation; regioselective reaction;	83%

tetrahydrofuran-3-one (22929-52-8) + ethylamine (75-04-7) → N-ethyltetrahydrofuran-3-amine

Conditions	Yield
Stage #1: tetrahydrofuran-3-one; ethylamine With sodium tetrahydroborate In tetrahydrofuran; methanol at 20℃; for 16h; Molecular sieve; Stage #2: With methanol; sodium tetrahydroborate In tetrahydrofuran at 0 - 20℃; for 2h;	83%

tetrahydrofuran-3-one (22929-52-8) + 1-bromo-4-methoxy-benzene (104-92-7) → 3-(4-methoxyphenyl)tetrahydrofuran-3-ol

Conditions	Yield
Stage #1: 1-bromo-4-methoxy-benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.416667h; Inert atmosphere; Stage #2: tetrahydrofuran-3-one In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Inert atmosphere;	82%

Upstream product

• 453-20-3 3-Hydroxytetrahydrofuran 
• 1191-99-7 2,3-dihydro-2H-furan 
• 57595-23-0 methyl 4-oxotetrahydrofuran-3-carboxylate 
• 89898-51-1 ethyl tetrahydrofuran-3-one 4-carboxylate 
• 927-74-2 3-Butyn-1-ol 
• 1708-29-8 2,5-dihydrofuran 
• 29212-66-6 3-hydroxyfuran 

Downstream Products

• 102654-25-1 3-phenyltetrahydrofuran-3-ol 
• 3187-96-0 dihydro-furan-3-one-(2,4-dinitro-phenylhydrazone) 
• 453-20-3 3-Hydroxytetrahydrofuran 
• 17517-50-9 9-phenyl-2,3-dihydro-furo[3,2-b]quinoline 
• 106183-61-3 3-morpholino-4,5-dihydrofuran 
• 106183-62-4 4-(2,5-Dihydro-furan-3-yl)-morpholine 
• 130722-40-6 3-[3-(Naphthalen-2-ylmethoxy)-phenyl]-tetrahydro-furan-3-ol 
• 137344-86-6 1-ethynyl-3-oxacyclopentanol 
• 81866-98-0 7-oxa-1,3-diazaspiro[4.4]nonane-2,4-dione 
• 503551-88-0 methanesulfonic acid 2,6-dioxaspiro[4.5]dec-9-yl ester 
• 1036969-36-4 ethyl 3-[[(trans-4-methylcyclohexyl)carbonyl](tetrahydro-3-furanyl)amino]-1-(phenylmethyl)-1H-pyrazole-4-carboxylate 
• 865869-67-6 ethyl 1-(phenylmethyl)-3-[(tetrahydro-3-furanyl)amino]-1H-pyrazole-4-carboxylate 
• 1044507-03-0 3-(4-bromophenyl)-7-oxa-1,4-diazaspiro[4.4]nonan-2-one 
• 693247-48-2 C₂₂H₂₈F₆N₂O₂ 

Relevant academic research and scientific papers

Synthesis method of tetrahydrofuran-3-ketone

The invention discloses a synthesis method of tetrahydrofuran-3-ketone. The method comprises the following steps of: under an alkaline condition, mixing glycolate (I) and acrylate (II) in a solvent, and carrying out condensation cyclization reaction to obtain 4-formic ester-tetrahydrofuran-3-ketone (III); then, under an acidic condition, performing reflux decarboxylation reaction on the 4-formic ester-tetrahydrofuran-3-ketone (III) so as to obtain thetetrahydrofuran-3-ketone (IV) . According to the synthesis method of the tetrahydrofuran-3-ketone, the yield is greater than 82%; and the method has the advantages of mild and easily-controlled conditions, mild reaction, simple and safe operation and environmental friendliness.

Gold-Catalyzed Oxidative Cyclization/Aldol Addition of Homopropargyl Alcohols with Isatins

A novel gold-catalyzed oxidative cyclization/aldol addition of homopropargyl alcohols with isatins has been developed that provides an effective access to the 3-hydroxyoxindoles in high yields under mild reaction conditions with high diastereoselectivities. In comparison with disclosed transformations of alkyne oxidations via an α-oxo gold carbene route, this is the first example of an aldol-type interception of an ylide (or its enolate form) intermediate with alkyne as a safe and readily available nondiazo carbene precursor.

COMPOUNDS FOR TREATMENT OF GLIOBLASTOMA

The present invention relates to compounds and methods for the treatment of glioblastoma, as well as to a pharmaceutical composition comprising said compounds. More specifically the invention relates to substituted quinoline derivatives having the formula (I), (II) or (III), and a pharmaceutical composition comprising said compounds for the treatment of cancer. (Formulae (I), (II), (III))

NOVEL PROCESS FOR THE MANUFACTURE OF 3-OXO-TETRAHYDROFURAN

This invention relates to a novel method for the preparation of 3-oxotetrahydrofuran comprising oxidating 3-hydroxy-tetrahydrofuran in the presence of a catalytic amount of TEMPO with trichloroisocyanuric acid.

NOVEL PROCESS FOR THE MANUFACTURE OF 3-OXO-TETRAHYDROFURAN

This invention relates to a novel method for the preparationof 3-oxotetrahydrofurancomprising oxidating 3-hydroxy-tetrahydrofuran in the presence of a catalytic amount of TEMPO with trichloroisocyanuric acid.

NOVEL PROCESS FOR THE MANUFACTURE OF 3-OXO-TETRAHYDROFURAN

This invention relates to a novel method for the preparation of 3-oxo-tetrahydrofuran comprising oxidizing 3-hydroxy-tetrahydrofuran in the presence of a catalytic amount of 2,2,6,6-tetramethyl-piperidine-N-oxyl (TEMPO) with trichloroisocyanuric acid.

3-PYRIDYL CARBOXAMIDE-CONTAINING SPLEEN TYROSINE KINASE (Syk) INHIBITORS

The invention provides certain 3-pyridyl carboxamide-containing compounds of the Formula (I) (I) or pharmaceutically acceptable salts thereof, wherein A and B are as defined herein. The invention also provides pharmaceutical compositions comprising such compounds, and methods of using the compounds for treating diseases or conditions mediated by Spleen Tyrosine Kinase (Syk) kinase.

2-PYRIDYL CARBOXAMIDE-CONTAINING SPLEEN TYROSINE KINASE (SYK) INHIBITORS

The invention provides certain 2-pyridyl carboxamide-containing compounds of the Formula (I) or pharmaceutically acceptable salts thereof, wherein A and B are as defined herein. The invention also provides pharmaceutical compositions comprising such compounds, and methods of using the compounds for treating diseases or conditions mediated by Spleen Tyrosine Kinase (Syk) kinase.

SPIROHYDANTOIN COMPOUNDS AND THEIR USE AS SELECTIVE ANDROGEN RECEPTOR MODULATORS

The present invention relates to a compound of formula (1-1 ) in free form or in pharmaceutically acceptable salt form in which the substituents are as defined in the specification; to its preparation, to its use as a medicament and to medicaments comprising it. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

HIV Integrase Inhibitors

The invention encompasses a series bicyclic pyrimidinone compounds of Formula I which inhibit HIV integrase and prevent viral integration into human DNA. This action makes the compounds useful for treating HIV infection and AIDS. The invention also encompasses pharmaceutical compositions and methods for treating those infected with HIV.