ChemicalBook CAS DataBase List Hexanoic acid, 3-oxo-6-(phenylmethoxy)-, ethyl ester

Hexanoic acid, 3-oxo-6-(phenylmethoxy)-, ethyl ester synthesis

6synthesis methods

Product Name:Hexanoic acid, 3-oxo-6-(phenylmethoxy)-, ethyl ester
CAS Number:10378-08-2
Molecular formula:C15H20O4
Molecular Weight:264.32

10385-30-5
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6148-64-7 Synthesis

6148-64-7
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Hexanoic acid, 3-oxo-6-(phenylmethoxy)-, ethyl ester

10378-08-2
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Yield:10378-08-2 86%

Reaction Conditions:

with triethylamine;1,1'-carbonyldiimidazole;magnesium chloride in acetonitrile at 90; for 2 h;

Steps:

^IV.^E^{thyl 6}^-benzyloxy^{-4,4-dimethyl-3-oxohexan}^{oate (}^8b⁾

General procedure: To a solution of methyl 4-benzyloxy-2,2-dimethylbutanoate 7b (4.0 g, 17 mmol) in methanol (25 ml) was added 1.0 N NaOH (25 mL, 25 mmol) at room temperature, and the mixture was warmed to 50 ^oC. After stirring at 50 ^oC for 3 hours, the solvent was removed under vacuum. The residue was diluted with water and CHCl₃, and the two layers were separated. The aqueous layer was acidified with 1.0 N HCl to pH = 3, then extracted with EtOAc, and washed with aq. NaCl. The combined organic layer was dried over Na₂SO₄ and concentrated in vacuo. The residue was dissolved in CH₃CN (34 mL), and added carbonyl diimidazole (2.9 g, 18 mmol) at room temperature (solution A). To a solution of MgCl₂ (3.5 g, 37 mmol) in CH₃CN (34 mL) was added potassium 3-ethoxy-3-oxopropanoate (6.1 g, 36 mmol) and triethylamine (11 mL, 76 mmol) at room temperature. After stirring at ambient temperature for 14 hours, the mixture was added ‘‘solution A’’ slowly, then warmed to 90^oC. After stirring at 90 ^oC for 2 hours, cooled to room temperature, then the mixture was acidified with 1.0 N HCl to pH = 5, extracted with EtOAc, and washed with aq. NaCl. The combined organic layer was dried over Na₂SO₄ and concentrated in vacuo. The residue was purified with column chromatography (silica gel, eluting with hexane/EtOAc) to give the title compound as a colorless oil (4.7 g, 95 % yield).

References:

Udagawa, Shuji;Sakami, Satoshi;Takemura, Takahiro;Sato, Mikiya;Arai, Takahiro;Nitta, Aiko;Aoki, Takumi;Kawai, Koji;Iwamura, Tomokatsu;Okazaki, Seiji;Takahashi, Takehiro;Kaino, Mie [Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,# 6,p. 1617 - 1621] Location in patent:supporting information

1462-37-9 Synthesis