Tetrahydrofuran → HCID 57656047, compound

HRID 911650Notes

Reaction equation

HRID 911650 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 96.5%

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 (3 g, 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-84ab6714dd3b4f388ca00f55f31546c0
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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