2,2-Dimethyl-1,3-dioxane-4,6-dione → HCID 19887633, compound

To a solution of acid from Step 1 (1.048 g, 5 mmol) in CH2Cl2 (45 mL) at r.t. there was added oxalyl chloride (762 mg, 6 mmol) and 2 drops of DMF. The mixture was stirred at r.t. for 1 hour, then it was added slowly to a cooled (0° C.) solution of 2,2-dimethyl-1,3-dioxan-4,6-dione (864 mg, 6 mmol) in CH2Cl2 (10 mL) and pyridine (1 mL). The resulting mixture was stirred at 0° C. for 30 minutes, then at r.t. for 1.5 hours. The CH2Cl2 was evaporated, there was added a mixture of HOAc (15 mL) and H2O (30 mL), and the mixture was heated at 90° C. for 45 minutes. After dilution with H2O, the mixture was extracted twice with EtOAc, and these combined extracts were washed with H2O, dried and evaporated to a residue which was chromatographed on silica gel, eluting with EtOAc-hexane (1:2) to afford the title compound as a yellow oil.

1. additionit was added slowly to
2. stirringThe resulting mixture was stirred at 0° C. for 30 minutes
3. waitat r.t. for 1.5 hours
4. customThe CH2Cl2 was evaporated
5. additionthere was added
6. additiona mixture of HOAc (15 mL) and H2O (30 mL)
7. temperaturethe mixture was heated at 90° C. for 45 minutes
8. extractionAfter dilution with H2O, the mixture was extracted twice with EtOAc
9. washthese combined extracts were washed with H2O
10. customdried
11. customevaporated to a residue which
12. customwas chromatographed on silica gel
13. washeluting with EtOAc-hexane (1:2)

ORD record

ord-eb197785796a4600bcaaa63e6c0a6585

Source dataset

uspto-grants-1992_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05132319