Borane;tetrahydrofuran → HCID 178419171, compound

HRID 2361551Notes

Reaction equation

HRID 2361551 reaction equation
[CH3:1][N:2]([CH3:24])[C:3]1[C:8]([CH3:9])=[CH:7][C:6]([PH:10](=O)[C:11]2[CH:16]=[C:15]([CH3:17])[C:14]([N:18]([CH3:20])[CH3:19])=[C:13]([CH3:21])[CH:12]=2)=[CH:5][C:4]=1[CH3:23].[BH3:25].O1CCCC1>C1(C)C=CC=CC=1>[CH3:24][N:2]([CH3:1])[C:3]1[C:8]([CH3:9])=[CH:7][C:6]([PH:10][C:11]2[CH:16]=[C:15]([CH3:17])[C:14]([N:18]([CH3:19])[CH3:20])=[C:13]([CH3:21])[CH:12]=2)=[CH:5][C:4]=1[CH3:23].[BH3:25]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 178429638HCID 178429638, compound

Product 1

HCID 178419171HCID 178419171, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under an argon atmosphere, to a solution of bis(4-dimethylamino-3,5-dimethylphenyl)phosphine oxide (4.6 g, 14 mmoL) synthesized in Example 1 in toluene (30 mL) was added borane-tetrahydrofuran solution (71 mL, 5.4 equivalents) at room temperature over 2 hr. Then, silica gel (8.7 g, 10.8 equivalents) was added to the mixture, and the mixture was stirred at room temperature for 1.5 hr. The silica gel was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel 20 g, toluene) and the residue was recrystallized from n-hexane to give the title compound (3.0 g, white crystals). yield 65%.

Workup

  1. additionThen, silica gel (8.7 g, 10.8 equivalents) was added to the mixture
  2. customThe silica gel was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by column chromatography (silica gel 20 g, toluene)
  5. customthe residue was recrystallized from n-hexane

Sources & evidence

ORD record
ord-d98369f6a861487391372bcf42d5aff4
Source dataset
uspto-grants-2014_04
Patent number
US08691718B2

Reaction notes

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