Tetrahydrofuran → HCID 57656047, compound

HRID 2041514Notes

Reaction equation

HRID 2041514 reaction equation
C1COCC1.[CH3:6][C:7]([CH3:20])([CH3:19])[CH2:8][O:9][CH2:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1.[H][H]>CO>[CH3:6][C:7]([CH3:20])([CH3:19])[CH2:8][O:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][NH2:16])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 59019312HCID 59019312, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57656047HCID 57656047, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add 1M BH3-THF complex in THF (16 mL, 16 mmol) to neat 4-(2,2-dimethyl-propoxymethyl)-benzonitrile (3.043 g, 15 mmol) and stir the mixture overnight at room temperature. Add methanol and stir until hydrogen evolution stops. Concentrate the solution in vacuo. Dissolve the crude mixture in methanol and filter through an SCX column eluting with methanol followed by 3M ammonia in methanol. Concentrate in vacuo to obtain the title compound (3g, 96%).

Workup

  1. concentrationConcentrate the solution in vacuo
  2. dissolutionDissolve the crude mixture in methanol
  3. filtrationfilter through an SCX column
  4. washeluting with methanol
  5. concentrationConcentrate in vacuo

Sources & evidence

ORD record
ord-3ed2461cbeee49349af3783d7824b202
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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