Diethyl Ether → HCID 20145924, compound

HRID 418910Notes

Reaction equation

HRID 418910 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[CH2:15][C:16]#N.[H-].C([Al+]CC(C)C)C(C)C.CC[O:30]CC>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[CH2:15][CH:16]=[O:30]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 21225700DiisobutylaluminumhydrideHCID 66651716HCID 66651716, compound

Product 1

HCID 20145924HCID 20145924, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Combine [2-(2-methoxy-phenyl)-cyclohexyl]-acetonitrile (0.346 g, 1.51 mmol), diisobutylaluminum hydride (2.7 mL, 2.72 mmol), and ether (8.0 mL) at −10° C. After 1 hour quenched reaction at 0° C. with 1N HCl and added ethyl acetate. Separate layers, wash with brine, and dry over anhydrous sodium sulfate. Concentrate to yield the titled compound (0.336 g, 96%). TLC Rf=0.08 in 5% ethyl acetate/hexanes. 1H NMR (CDCl3): 9.3 (s, 1H), 7.2 (m, 1H), 7.0 (m, 1H), 6.9 (m, 2H), 3.8 (s, 3H), 3.3 (m, 1H), 2.8 (m, 1H), 2.3 (m, 1H), 2.2 (m, 2H), 1.6 (m, 7H).

Workup

  1. customat −10° C
  2. customAfter 1 hour quenched
  3. customreaction at 0° C. with 1N HCl
  4. washSeparate layers, wash with brine
  5. dry with materialdry over anhydrous sodium sulfate
  6. concentrationConcentrate

Sources & evidence

ORD record
ord-6004d20668f449c8a858855183f3db9b
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

Loading…