Ethyl formate → HCID 15023379, compound

To 20 ml of an ethereal suspension of 1.20 g (30 mmol) of 60% sodium hydride was added dropwise 20 ml of an ethereal solution of 7.42 g (20 mmol) of ethyl γ-ketooctadecanoate ethylene ketal prepared in Synthetic Example 3 and 1.93 g (26 mmol) of ethyl formate under stirring at room temperature. The mixture was stirred at room temperature for 18 hours. Then, 0.70 g (17 mmol) of 60% sodium hydride and 1.00 g (13 mmol) of ethyl formate were further added to the mixture and the whole was stirred at the room temperature for 50 hours. The reaction was terminated by adding diluted hydrochloric acid and the resulting mixture was extracted with ether. A residue obtained by removing the solvent from the extract under reduced pressure was treated with 30 ml of concentrated hydrochloric acid under vigorous stirring for 1.5 hours. The resulting mixture was extracted with ether, washed with a saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After removing the solvent under a reduced pressure, the residue was purified by subjecting it to column chromatography over silica gel (eluent: ethyl acetate/hexane=1/10) to obtain 3.63 g (51% yield) of ethyl γ-keto-α-formyloctadecanoate.

1. stirringThe mixture was stirred at room temperature for 18 hours
2. stirringthe whole was stirred at the room temperature for 50 hours
3. customThe reaction was terminated
4. additionby adding diluted hydrochloric acid
5. extractionthe resulting mixture was extracted with ether
6. customA residue obtained
7. customby removing the solvent from the
8. extractionextract under reduced pressure
9. additionwas treated with 30 ml of concentrated hydrochloric acid
10. stirringunder vigorous stirring for 1.5 hours
11. extractionThe resulting mixture was extracted with ether
12. washwashed with a saturated sodium chloride solution
13. dry with materialdried over anhydrous magnesium sulfate
14. customAfter removing the solvent under a reduced pressure
15. customthe residue was purified

ORD record

ord-a894158ea50f45918fcb1f2d68869502

Source dataset

uspto-grants-1995_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

USRE035096