Hydrochloric Acid → HCID 54304054, compound

Temperature

5 °C

A cooled (-20° C.) solution of 8-ketotricyclo[5.2.1.0]decane (7.51 g, 50 mmol) in anhydrous tetrahydrofuran (50 mL) under nitrogen was treated with n-butyl nitrite (6.70 mL, 5.92 g, 57.3 mmol), then with solid potassium t-butoxide (11.22 g, 100 mmol) in portions at a rate to keep the pot temperature below -10° C. The red mixture was stirred at -10° C. for one h and at 5° C. for 3.5 h, then it was quenched by addition to ice water (125 mL). The mixture was treated with concentrated hydrochloric acid (11 mL, 132 mmol), then the aqueous solution was extracted with methylene chloride (150 mL, then 2×100 mL). The combined organic solution was washed with saturated aqueous sodium bicarbonate (2×100 mL), water (100 mL), dried (Na2SO4), and concentrated in vacuo. The residue was chromatographed on silica gel (eluted with 5% acetone/methylene chloride) to afford tricyclo[5.2.1.0 (2,6)]decan-8,9-dione, oxime (4.88 g, 54.5%) as a white solid.

1. customthe pot temperature below -10° C
2. customit was quenched by addition to ice water (125 mL)
3. extractionthe aqueous solution was extracted with methylene chloride (150 mL
4. washThe combined organic solution was washed with saturated aqueous sodium bicarbonate (2×100 mL), water (100 mL)
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated in vacuo
7. customThe residue was chromatographed on silica gel (eluted with 5% acetone/methylene chloride)

ORD record

ord-c07b735368c94504aa3c1e91a6d47bb9

Source dataset

uspto-grants-1996_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05583221