Diethyl Ether → HCID 85971407, compound

HRID 530239Notes

Reaction equation

HRID 530239 reaction equation
[CH3:1][C:2]1[CH2:6][CH2:5][C:4]([CH3:8])([CH3:7])[C:3]=1[C:9]#N.[H-].C([Al+]CC(C)C)C(C)C.C([O:23]CC)C>ClCCl>[CH3:1][C:2]1[CH2:6][CH2:5][C:4]([CH3:8])([CH3:7])[C:3]=1[CH:9]=[O:23]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 21225700DiisobutylaluminumhydrideHCID 217652822,5,5-Trimethylcyclopent-1-ene-1-carbonitrile

Product 1

HCID 85971407HCID 85971407, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the product of Example 8g (600 mg, 4.44 mmol) in anhydrous dichloromethane (30 mL) at −78° C. under argon was added diisobutyl aluminum hydride (1.0 M in hexane, 8.9 mL, 8.9 mmol). The reaction was kept at −78° C. for 2 hours. The mixture was diluted with diethyl ether (150 mL) and quenched by addition of wet sodium sulfate. The mixture was then stirred for 30 minutes, filtered and the filtrate concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate=50/1->20/1) to afford the title compound as a light yellow liquid (420 mg, Yield: 68%). 1H NMR (400 MHz, CDCl3) δ 9.98 (s, 1H), 2.45 (t, J=7.4 Hz, 2H), 2.10 (s, 3H), 1.67 (t, J=7.4 Hz, 2H), 1.22 (s, 6H) ppm.

Workup

  1. customquenched by addition of wet sodium sulfate
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate=50/1->20/1)

Sources & evidence

ORD record
ord-a1a5d71c83d0497983eee72486e73be8
Source dataset
uspto-grants-2016_05
Patent number
US09353063B2

Reaction notes

Loading…