10226-28-5

Basic information

• Product Name: 3-ETHOXYCARBONYL-5,6-DIHYDRO-2-METHYL-4H-PYRAN
• Synonyms: 5,6-Dihydro-3-ethoxycarbonyl-2-methyl-4H-pyran;ethoxycarbonyl?ihydromethylpyran;3-ETHOXYCARBONYL-2-METHYL-5,6-DIHYDRO-4H-PYRAN;3-ETHOXYCARBONYL-5,6-DIHYDRO-2-METHYL-4H-PYRAN;3-ETHOXYCARBONYL-5,6-DIHYDRO-2-METHYL-4H-PYRANE;ETHYL 6-METHYL-3,4-DIHYDRO-2H-PYRAN-5-CARBOXYLATE;ethyl 3,4-dihydro-6-methyl-2H-pyran-5-carboxylate;3-ETHOXYCARBONYL-5,6-DIHYDRO-2-METHYL-4H-PYRANE 95+%
• CAS NO: 10226-28-5
• Molecular Formula: C₉H₁₄O₃
• Molecular Weight: 170.21
• EINECS: 233-543-9
• Product Categories: Heterocycles;Miscellaneous Reagents
• Mol File: 10226-28-5.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 217 °C
• Flash Point: 89.2 °C
• Appearance: /
• Density: 1.07
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-ETHOXYCARBONYL-5,6-DIHYDRO-2-METHYL-4H-PYRAN(CAS DataBase Reference)
• NIST Chemistry Reference: 3-ETHOXYCARBONYL-5,6-DIHYDRO-2-METHYL-4H-PYRAN(10226-28-5)
• EPA Substance Registry System: 3-ETHOXYCARBONYL-5,6-DIHYDRO-2-METHYL-4H-PYRAN(10226-28-5)

Safety Data

• Statements: 10
• Safety Statements: 16
• RIDADR: 3272
• Hazardous Substances Data: 10226-28-5(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Oil

Uses

2-Methyl-3-carbethoxy-5,6-dihydropyran (cas# 10226-28-5) is a compound useful in organic synthesis.

Synthesis Reference(s)

Journal of the American Chemical Society, 68, p. 1294, 1946 DOI: 10.1021/ja01211a052

Upstream product

• 1007476-32-5 sodium ethyl acetylacetate enolate 
• 109-64-8 1,3-dibromo-propane 
• 141-97-9 ethyl acetoacetate 
• 109-70-6 1.3-chlorobromopropane 
• 14749-45-2 ethyl 2-(3-chloropropyl)acetoacetate 
• 570-08-1 diethyl acetylmalonate 
• 75-03-6 ethyl iodide 

Downstream Products

• 21856-89-3 6-hydroxy-2-hexanone 
• 10226-29-6 6-Bromo-2-hexanone 
• 15719-64-9 methylammonium carbonate 
• 20210-14-4 2-(4-Bromobutyl)-2-methyl-1,3-dioxolane 
• 324012-40-0 (3aS,6aR)-1,3-Dibenzyl-4-(5-oxohexylidene)tetrahydro-1H-thieno[3,4-d]imidazole-2(3H)-one 
• 1417917-85-1 N-(2,4-dimethoxybenzyl)-3,4-dihydro-2H-pyrano[2,3-d]pyridazin-5-amine 
• 1417917-57-7 N-(3,4-dihydro-2H-pyrano[2,3-d]pyridazin-5-yl)-2-(3-(4-(4-methoxybenzoyl)piperidin-1-yl)-2-oxopyrrolidin-1-yl)acetamide 
• 1643935-92-5 phenyl (S)-3-hydroxy-4-(3-hydroxypropyl)-1-methyl-5-methylene-2-oxocyclopent-3-ene-1-carboxylate 
• 1643935-77-6 (E)-phenyl 3-(benzhydryloxy)-2-methyl-4-(6-methyl-3,4-dihydro-2H-pyran-5-yl)-4-oxobut-2-enoate 
• 5399-21-3 6-methyl-3,4-dihydro-2H-pyran-5-carboxylic acid 

Relevant articles and documents

A one-step synthesis of tetrahydropyranopyranones from carbonyl compounds

A one-step synthesis of tetrahydropyranopyranones, a ring system present in the natural product FR182877, from carbonyl compounds is described.

An efficient and enantioselective synthesis of d-biotin

An efficient and enantioselective synthesis of d-biotin 1 starting from cis-1,3-dibenzyl-2-imidazo-lidone-4,5-dicarboxylic acid (6) is described. The key steps are the enantioselective reduction of meso-1,2-dicarboxylic thioanhydride 8 to prepare the (3as, 6ar)- thiolactone 9 and the introduction of the C6 side chain at C-2 in 9 via a modified Grignard reaction. This novel synthesis proceeded in six steps to afford 1 with 21% overall yield.

Metal ion effects on the rate of intramolecular O-alkylation of the anion of ethyl(3-chloropropyl)acetoacetate

The retarding effect of alkali metal and alkaline-earth metal ions on the rate of intramolecular O-alkylation of the title compound has been thoroughly investigated in 99% aqueous Me2SO at 25°C. Rate data have been dissected into contributions of free ions (ki) and ion pairs (kip). Comparison of the present results with available data for intramolecular C-alkylation of a strictly related system, reveals that rate-depressing effects due to cation pairing turn out to be remarkably similar in the two processes, which is at variance with the expectation of a more pronounced cation dependence of the kip/ki ratios for O-alkylation than for C-alkylation.