2-Acetylbutyrolactone

Colorless to light yellow liqui

An intermediate in the synthesis of 2,4-disubstituted pyridines. A fluorogenic reagent for the spectrofluorimetric determination of primary amines.

Liquid

3-Acetyldihydro-2(3H)-furanone is a gamma-lactone.

At 5 °C, a solution of MAA (46.9 g 0.40 mol) in MeOH (144.0 g) was treated with EO (25.0 g, 1.4 eq.) and then with triethylamine (TEA, 40.7 g, 1.0 eq.). The reaction mixture was heated to 60 °C within 0.5 h and kept at this temperature for 2.5 h. Quantitative GC analysis indicated that 50.8percent of MAA had been transformed into ABL with a selectivity of 72.9percent. At 5 °C, a solution of methyl acetoacetate (MAA, 46.7 g, 0.40 mol) in methanol (MeOH, 144.0 g) was treated with ethylene oxide (EO, 17.5 g, 1.0 eq.) and then with 1, 1, 3, 3-tetramethylguanidine (TMG, 46.1 g, 1.0 eq.). The reaction mixture was heated to 40 °C within 0.5 h and kept at this temperature for 4.5 h. Quantitative GC analysis indicated that 53.7percent of MAA had been transformed into α-acetylbutyrolactone (ABL) with a selectivity of 75.2percent.Examples 7-27: The process of example 1, by using an EO amount, optionally a catalyst at an amount as described in Table 1, and an additive at an amount as described in Table 1, and a reaction time as described in Table 1. Turnover and selectivity as described in Table 1.(1) The reactor slow heating to 75 °C, adding γ - butyrolactone, ethyl acetate and sodium ethoxide, reflux reaction 10 h after, shall be α - acetyl - γ - butyrolactone sodium salt and the by-product ethanol, wherein γ - butyrolactone and ethyl acetate increase mole ratio of 1:4, γ - butyrolactone and sodium ethoxide in a molar ratio of 1: 1.4;(2) Step (1) the resultant product distillation, to remove the excess of ethanol and ethyl acetate, the residue is dissolved in dilute sulfuric acid to adjust the pH to 4, standing minute fluid minute to the aqueous phase, the organic phase in the pressure is -0.1 mpa, temperature is 70 °C under the condition of reduced pressure distillation shall be α - acetyl γ - butyrolactone.100 g of ethyl acetate was added to a 500 ml reaction flask, and after warming to 50 ° C, 80 g of solid sodium methoxide was added simultaneously.The mixture was mixed with 86 g of ethyl acetate and 100 g of γ-butyrolactone, and the temperature of the system was maintained at 50 ° C, and the addition was completed within 2 hours. After the addition of the material, stirring was continued rapidly for 1 h at 60 °C. Discharge, the above liquid material is added to a 500ml autoclave, high pressure reaction at 100 ° C for 2h, the pressure gauge shows a small pressure, the pressure range is 0.1-1MPa, the reaction is completed, cooling, discharge, using 20g ethyl acetate wash reaction The kettle and the washing liquid were combined into the reaction liquid and used. The above materials were transferred to a 500 ml reaction flask, distilled under reduced pressure at 60 ° C (vacuum degree 0.09 MPa - 0.1 MPa), and concentrated to near dryness. The precipitated solid was a solid of α-acetyl-γ-butyrolactone sodium salt.The material was washed with 280 ml of ethyl acetate in a solid of α-acetyl-γ-butyrolactone sodium salt, filtered, and washed twice.Adding 260 ml of ethyl acetate to the above α-acetyl-γ-butyrolactone sodium salt solid.Cooling, temperature control at -5-5 °C, withThe 70percent ethyl acetate solution was adjusted to pH 6-7, stirred for 5 hours, filtered, and the filter cake was washed with 20 ml of ethyl acetate. The filtrate was transferred to a 500 ml single-mouth bottle and distilled under reduced pressure at 70 ° C (vacuum degree 0.09 MPa - 0.1 MPa). After the low-boiling substance was distilled, the concentrated liquid in the bottle was further heated to 95 ° C under reduced pressure (vacuum degree). ≤ 50 Pa), 104.7 g of α-acetyl-γ-butyrolactone was obtained, and the purity was 98.7percent, and the yield was 83.0percent by gas chromatography.

An intermediate in the synthesis of 2,4-disubstituted pyridines. A fluorogenic reagent for the spectrofluorimetric determination of primary amines.

Intermediates

10,000,000 - 50,000,000 lb

Molecular Weight:128.13
XLogP3:0.1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:128.047344113
Monoisotopic Mass:128.047344113
Topological Polar Surface Area:43.4
Heavy Atom Count:9
Complexity:150
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes