ChemicalBook CAS DataBase List 2,2-DIMETHYL-1,3-DIOXAN-5-ONE

2,2-DIMETHYL-1,3-DIOXAN-5-ONE synthesis

5synthesis methods

Product Name:2,2-DIMETHYL-1,3-DIOXAN-5-ONE
CAS Number:74181-34-3
Molecular formula:C6H10O3
Molecular Weight:130.14

53104-32-8 Synthesis

(5-AMINO-2,2-DIMETHYL-[1,3]DIOXAN-5-YL)-METHANOL

53104-32-8
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$60.00/50mg

74181-34-3
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$13.00/100mg

Yield:74181-34-3 91%

Reaction Conditions:

with sodium periodate;potassium dihydrogenphosphate in water at 0 - 20; for 4 h;

Steps:

2.1 4.2.1. 2,2-Dimethyl-1,3-dioxane-5-one (8)
2,2-Dimethoxypropane (21.5 mL, 175 mmol) and p-toluenesulfonic acid monohydrate (1.58 g, 7.93 mmol) were added to a solution of tris(hydroxylmethyl)aminomethane (25.2 g, 159 mmol) inDMF (180 mL), and the mixture was stirred at room temperaturefor 22 h. The mixture was diluted with ethyl acetate, and then triethylamine was further added. The solvent was removed underreduced pressure, then the crude product was purified with silicagel column chromatography (eluent; n-hexane/ethyl acetate; 5:1)to give 2,2-dimethyl-5-amino-5-hydroxymethyl-1,3-dioxaone(20.9 g, 78%) as colorless solid. 2,2-Dimethyl-5-amino-5-hydroxymethyl-1,3-dioxaone: 1H NMR (400 MHz, CDCl3) d 3.80 (d,J = 12.0 Hz, 2H), 3.60 (d, J = 12.0 Hz, 2H), 3.53 (s, 2H), 2.61 (s, 2H),1.45 (s, 3H), 1.41 (s, 3H). The obtained intermediate (10.2 g,62.1 mmol) was dissolved in water (60 mL), and KH2PO4 (8.51 g,621 mmol) was added to the solution. Then aqueous solution ofNaIO4 (0.5 M, 125 mL, 63 mmol) was added dropwise during 3 hat 0 C and then stirred for 1 h at room temperature. The mixturewas extracted with dichloromethane and the organic layer waswashed with 5% aqueous sodium thiosulfate and brine and driedwith Na2SO4. The solvent was removed under reduced pressureto give compound 8 (7.35 g, 91%) as colorless oil. 1H NMR(400 MHz, CDCl3) d 4.15 (s, 4H), 1.45 (s, 6H).

References:

Fujii, Shinya;Sekine, Ryota;Kano, Atsushi;Masuno, Hiroyuki;Songkram, Chalermkiat;Kawachi, Emiko;Hirano, Tomoya;Tanatani, Aya;Kagechika, Hiroyuki [Bioorganic and Medicinal Chemistry,2014,vol. 22,# 21,p. 5891 - 5901] Location in patent:supporting information

FullText

3391-30-8 Synthesis