Sulfuric Acid → HCID 86652437, compound

Temperature

0 °C

The reaction was carried out in a procedure similar to that described in Tetrahedron, 50(9), 2821-30; 1994: To a solution of 1-[(trimethylsilyl)oxy]cyclopentanecarbonitrile (2.25 g, 12.3 mmol, prepared as described in Organometallics, 3(11), 1660-5; 1984) in toluene (18 mL) at −45° C. was added dropwise 1.0 M of diisobutylaluminum hydride in hexane (17.2 mL, 17.2 mmol). The solution was then allowed to warm to 0° C. and stir for 1 h at this temperature. The reaction mixture was poured into a mixture of diethyl ether (25 mL) and ammonium chloride (25 mL, saturated). To the resulting mixture, at 15° C., was added a dilute solution of sulfuric acid (prepared by diluting 1.53 mL of concentrated H2SO4 with 50 mL water). The solution was then stirred at a temperature of 5° C. overnight. The mixture was extracted with three portions of diethyl ether, the combined extracts were washed with brine, dried over sodium sulfate, decanted and concentrated to afford product (0.84 g, 36%), which was used without further purification in Step 2. 1H NMR (300 MHz, CDCl3): δ 9.47 (s, 1H), 1.88-1.46 (m, 8H), 0.00 (s, 9H).

1. stirringThe solution was then stirred at a temperature of 5° C. overnight
2. extractionThe mixture was extracted with three portions of diethyl ether
3. washthe combined extracts were washed with brine
4. dry with materialdried over sodium sulfate
5. customdecanted
6. concentrationconcentrated

ORD record

ord-834aac72177d4eba979b08795e97c9a6

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08486902B2