Tetrahydrofuran → HCID 20099906, compound

HRID 512010Notes

Reaction equation

HRID 512010 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=2)[C:18]#N)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.C1C[O:36]CC1>CCCCCC>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=2)[CH:18]=[O:36])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 200999373'-(Benzyloxy)[1,1'-biphenyl]-3-carbonitrileHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 20099906HCID 20099906, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a stirred solution of 75 (0.12 g, 0.42 mmol) in anhydrous THF (10 mL) at −78° C., under a nitrogen atmosphere was added diisobutylaluminum hydride (0.5 mL, 0-5 mmol, using a 1M solution in hexane) dropwise. The reaction mixture was stirred at the same temperature for 1 hour and then quenched by dropwise addition of potassium sodium tartrate (10% solution in water). The resulting mixture was warmed to room temperature, diluted with diethyl ether (20 mL) and stirred vigorously for 1 h. The organic phase was separated and the aqueous phase was extracted with diethyl ether. The combined organic layer was washed with brine, dried (MgSO4) and evaporated under reduced pressure. The residue obtained was purified by flash column chromatography on silica gel (20% diethyl ether-hexane) to give 76 (0.091 g, 75% yield) as a viscous liquid.

Workup

  1. customquenched by dropwise addition of potassium sodium tartrate (10% solution in water)
  2. additiondiluted with diethyl ether (20 mL)
  3. stirringstirred vigorously for 1 h
  4. customThe organic phase was separated
  5. extractionthe aqueous phase was extracted with diethyl ether
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated under reduced pressure
  9. customThe residue obtained
  10. customwas purified by flash column chromatography on silica gel (20% diethyl ether-hexane)

Sources & evidence

ORD record
ord-72901e627ee248cb8a1adc9e0e1f68c8
Source dataset
uspto-grants-2015_08
Patent number
US09102622B2

Reaction notes

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