Acetoacetic Acid → 3,5-Dioxohexanoic acid

A solution of the diacetate from stage (c) (7 g) in tetrahydrofuran (150 ml) was treated with tetra-n-butylammonium fluoride (1.4 g) at room temperature for 18 h. Tlc (ether/light petroleum, 6:1) showed one major product with traces of slow moving products due to partial deacetylation. The mixture was concentrated, taken up in dry pyridine (50 ml) and treated acetic anhydride (7 ml) at room temperature for 3 h. Tlc ether/light petroleum (7:1) showed only one product. The reaction mixture was concentrated and was eluted from short column of silica gel (50 g) with ether/light petroleum (1:1) to give a crystalline product (4.3 g, 85.2%) identical with the product from Route 1, m.p. 133°-134° [α]D20 +116.3° (c 1.0, CHCl3).

1. concentrationThe mixture was concentrated
2. additiontreated acetic anhydride (7 ml) at room temperature for 3 h
3. concentrationThe reaction mixture was concentrated
4. washwas eluted from short column of silica gel (50 g) with ether/light petroleum (1:1)

ORD record

ord-ef499541b7fb4d469f6415f2051cf5f7

Source dataset

uspto-grants-1983_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04405654