Ethyl Acetate → HCID 178419204, compound

Diethylphosphite-cyanoborane (7a) (1.15 g) and Me3SiI (4 equivalents) were taken in anhydrous CH3CN and were heated at reflux in the dark for 2 days. The solvent and excess Me3SiI were removed under reduced pressure. The residue was taken in CH2Cl2 /water (1:1, v/v, 50 ml) and was stirred at room temperature for 1.5 hours. The aqueous layer was separated and washed with CH2Cl2 until the organic layer was colorless. The water was evaporated at room temperature by passing a stream of air over the solution. The residue was taken in EtOAc and filtered to remove a solid. The filtrate was dried and the solvent was removed under reduced pressure to give an oil. Often, the EtOAc solution became dark colored, which could not be removed by treatment with charcoal. To remove this color, the EtOAc was removed and the whole work-up was repeated. The yield of light yellow oil was 0.49 g, 50.72%.

1. temperaturewere heated
2. temperatureat reflux in the dark for 2 days
3. customThe solvent and excess Me3SiI were removed under reduced pressure
4. customThe aqueous layer was separated
5. washwashed with CH2Cl2 until the organic layer
6. customThe water was evaporated at room temperature
7. filtrationfiltered
8. customto remove a solid
9. customThe filtrate was dried
10. customthe solvent was removed under reduced pressure
11. customto give an oil
12. customwhich could not be removed by treatment with charcoal
13. customTo remove this color
14. customthe EtOAc was removed

ORD record

ord-e287857f99b149daa9d053d9164a07bf

Source dataset

uspto-grants-1995_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05399732