Carbon Dioxide → HCID 178515905, compound

Under N2, a solution of 52 (2.25 g, 0.0082 mol) in CH2Cl2 (25 ml) was added dropwise to a dry-ice cooled solution of BBr3 (2.5 ml, d=2.65, 0.0265 mol) in CH2Cl2 (75 ml). After the addition, the solution was stirred at room temperature overnight and then treated dropwise with CH3OH (50 ml). After stirring overnight at room temperature, the solution was concentrated to dryness, the residue treated with 10% NaOH, the aqueous layer extracted with Et2O, the pH of the solution adjusted to 8.7 and concentrated to dryness. The residue was triturated with hot CH3OH, filtered, the filtrate concentrated to dryness and the residue chromatographed on silica gel. The product was eluted with 10% CH3OH--CHCl3 to yield 1.75 g (82%) of 53.

1. additionAfter the addition
2. stirringAfter stirring overnight at room temperature
3. concentrationthe solution was concentrated to dryness
4. additionthe residue treated with 10% NaOH
5. extractionthe aqueous layer extracted with Et2O
6. concentrationconcentrated to dryness
7. customThe residue was triturated with hot CH3OH
8. filtrationfiltered
9. concentrationthe filtrate concentrated to dryness
10. customthe residue chromatographed on silica gel
11. washThe product was eluted with 10% CH3OH

ORD record

ord-26bc7ee8673c4ece87be12d01342b287

Source dataset

uspto-grants-1987_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04642311