Sodium hydride → 3-(3,4-Dichloro-phenyl)-dihydro-furan-2-one

A mixture of 30 g (137 mmol) (3,4-dichloro-phenyl)-acetic acid methyl ester (commercially available), 6.47 g (151 mmol) NaH (55%) and 35.8 g (171 mmol) 2-(2-bromo-ethoxy)-tetrahydro-pyran in 100 mL DMF was stirred at room temperature for 17 h. The mixture was evaporated to dryness and partitioned between water and ethyl acetate. The combined organic phases were washed with NaCl aq., dried with Na2SO4 and evaporated. The residue was treated with 400 mL 4N HCl in dioxane in 250 mL methanol and stirred for 16 h at room temperature. The mixture was evaporated to dryness and subjected to column chromatography on silica eluting with a gradient formed from ethyl acetate and heptane. The combined product fractions were evaporated to yield 18.5 g (58%) of the title compound as yellow oil.

1. customThe mixture was evaporated to dryness
2. custompartitioned between water and ethyl acetate
3. washThe combined organic phases were washed with NaCl aq.
4. dry with materialdried with Na2SO4
5. customevaporated
6. additionThe residue was treated with 400 mL 4N HCl in dioxane in 250 mL methanol
7. stirringstirred for 16 h at room temperature
8. customThe mixture was evaporated to dryness
9. customformed from ethyl acetate and heptane
10. customThe combined product fractions were evaporated

ORDレコード

ord-9fc0c1dcde5d4847b6912de4bf1adbd4

出典データセット

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07592345B2