Acetic Acid → HCID 68838538, compound

Temperature

0 °C

To a 250-mL 3-necked flask, oven dried and equipped with a mechanical stirrer was charged with pyridinium dichromate (20.24 g, 53.80 mmol), molecular sieves (oven dried) and DCM (40 mL). The resulting slurry was cooled to 0° C. and to this slurry, acetic acid (which had been dried over molecular sieves, 1.61 g, 26.90 mmol) was charged. The resulting mixture was stirred for 30 minutes at 0° C. 9 (10 g, 29.89 mmol) in DCM (10 mL) was added to the reaction mixture over a period of 10 minutes. The resulting reddish colored reaction mixture was stirred for 2 hours at 0° C. After the reaction was completed, ethyl acetate (100 mL), acetonitrile (5 mL), and diatomaceous earth (Celite®, 5 g) were added sequentially, and the resulting mixture was stirred for 10 minutes. The slurry was filtered on a bed of diatomaceous earth (Celite®) to give a dark colored filtrate. The filtrate was washed with 5% aqueous NaHSO3 (2×250 mL) followed by water (100 mL). The organic layer was dried over magnesium sulfate and the solvent was concentrated in vacuo to give 9.5 g of the title compound as a dark transparent, brown oil.

1. customTo a 250-mL 3-necked flask, oven dried
2. customequipped with a mechanical stirrer
3. additionwas charged
4. stirringThe resulting reddish colored reaction mixture was stirred for 2 hours at 0° C
5. stirringthe resulting mixture was stirred for 10 minutes
6. filtrationThe slurry was filtered on a bed of diatomaceous earth (Celite®)
7. customto give a dark colored filtrate
8. washThe filtrate was washed with 5% aqueous NaHSO3 (2×250 mL)
9. dry with materialThe organic layer was dried over magnesium sulfate
10. concentrationthe solvent was concentrated in vacuo

ORD record

ord-bbde3d1044704366b9a99ce7281d5e4b

Source dataset

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07034152B2