Sodium Sulfite → Diethyl 2-acetamido-2-(4-formylbutyl)malonate

Diethyl 2-acetamido-2-pentenylmalonate (4.0 g) was dissolved in 210 ml of acetone and 3.3 g of N-methylmorpholine-N-oxide and 36 ml of a 1% aqueous osmium tetraoxide solution were added thereto. The mixture was stirred at room temperature for 2 hours. A solution of 700 mg of sodium sulfite in 20 ml of water was added thereto and the mixture was stirred for 15 minutes. The reaction mixture was concentrated and subjected to silica gel column chromatography using chloroform/methanol (10:1) as an eluent and a fraction having an Rf value: 0.3 (chloroform:methanol=10:1) was concentrated. The residue was dissolved in 630 ml of 1,4-dioxane and 70 ml of a 0.2M aqueous meta-sodium periodate solution was added thereto. The mixture was stirred at room temperature for 2 hours. The reaction mixture was filtrated, concentrated, extracted with ethyl acetate and washed with water. The hexane layer was dehydrated and concentrated to give 4.17 g of colorless, oily diethyl 2-acetamido-2-(4-formylbutyl)malonate.

1. stirringthe mixture was stirred for 15 minutes
2. concentrationThe reaction mixture was concentrated
3. concentrationwas concentrated
4. dissolutionThe residue was dissolved in 630 ml of 1,4-dioxane
5. addition70 ml of a 0.2M aqueous meta-sodium periodate solution was added
6. stirringThe mixture was stirred at room temperature for 2 hours
7. filtrationThe reaction mixture was filtrated
8. concentrationconcentrated
9. extractionextracted with ethyl acetate
10. washwashed with water
11. concentrationconcentrated

ORD record

ord-f48776cf16294fd69a48f8ea086913fd

Source dataset

uspto-grants-1999_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05952316