2,2-Dimethyl-1,3-dioxane-4,6-dione → HCID 67148305, compound

Temperature

100 °C

A mixture of 3-(tert-butyl-dimethyl-silanyloxymethyl)-4-chloro-benzaldehyde (1.84 g, 6.46 mmol), Meldrum acid (931 mg, 6.46 mmol), and formic acid-triethylamine 5:2 complex (1.62 mL, 23.4 mmol) in DMF (6.00 mL) was heated to 100° C. for 3.5 h. Meldrum acid (466 mg, 3.23 mmol) was added again, and the mixture was stirred for 1 h at 100° C. The mixture was allowed to cool to rt, and was diluted with a mixture of water and ice. The resulting mixture was extracted several times with EtOAc. The combined org. extracts were washed with water, dried over MgSO4, filtered, and the solvents were removed under reduced pressure. The residue was dissolved in Et2O, and the resulting mixture was extracted several times with aq. 1M NaOH. The combined aq. extracts were acidified to pH 2 with aq. 1M HCl, and this aq. mixture was extracted back with Et2O several times. The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Drying the residue under high vacuum yielded the crude title compound (1.20 g, 87%) that was used further without purification. LC-MS: tR=0.71 min.

1. temperatureto cool to rt
2. extractionThe resulting mixture was extracted several times with EtOAc
3. washextracts were washed with water
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. customthe solvents were removed under reduced pressure
7. dissolutionThe residue was dissolved in Et2O
8. extractionthe resulting mixture was extracted several times with aq. 1M NaOH
9. extractionthis aq. mixture was extracted back with Et2O several times
10. dry with materialextracts were dried over MgSO4
11. filtrationfiltered
12. customthe solvents were removed under reduced pressure
13. customDrying the residue under high vacuum

ORD record

ord-b8daed818c664f0ea29932971ab0b2cd

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07968720B2