Sulfuric Acid → HCID 86652437, compound
Reaction equation
[CH3:1][Si:2]([CH3:12])([CH3:11])[O:3][C:4]1([C:9]#N)[CH2:8][CH2:7][CH2:6][CH2:5]1.[H-].C([Al+]CC(C)C)C(C)C.CCCCCC.[Cl-].[NH4+].S(=O)(=O)(O)[OH:32]>C1(C)C=CC=CC=1.C(OCC)C>[CH3:1][Si:2]([CH3:12])([CH3:11])[O:3][C:4]1([CH:9]=[O:32])[CH2:8][CH2:7][CH2:6][CH2:5]1Participants
Conditions
- Temperature
- 0 °C
Procedure
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 in L, 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).
Workup
- stirringThe solution was then stirred at a temperature of 5° C. overnight
- extractionThe mixture was extracted with three portions of diethyl ether
- washthe combined extracts were washed with brine
- dry with materialdried over sodium sulfate
- customdecanted
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-b313922cbff744baaf9f5dff7127c321
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08748401B2
Reaction notes
Loading…