Borane;tetrahydrofuran → HCID 178419179, compound

HRID 875285Notes

Reaction equation

HRID 875285 reaction equation
[CH3:1][N:2]([CH3:32])[C:3]1[C:8]([CH:9]([CH3:11])[CH3:10])=[CH:7][C:6]([PH:12](=O)[C:13]2[CH:18]=[C:17]([CH:19]([CH3:21])[CH3:20])[C:16]([N:22]([CH3:24])[CH3:23])=[C:15]([CH:25]([CH3:27])[CH3:26])[CH:14]=2)=[CH:5][C:4]=1[CH:29]([CH3:31])[CH3:30].[BH3:33].O1CCCC1>C1(C)C=CC=CC=1>[CH3:32][N:2]([CH3:1])[C:3]1[C:8]([CH:9]([CH3:11])[CH3:10])=[CH:7][C:6]([PH:12][C:13]2[CH:18]=[C:17]([CH:19]([CH3:20])[CH3:21])[C:16]([N:22]([CH3:24])[CH3:23])=[C:15]([CH:25]([CH3:27])[CH3:26])[CH:14]=2)=[CH:5][C:4]=1[CH:29]([CH3:31])[CH3:30].[BH3:33]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 178439536HCID 178439536, compound

Product 1

HCID 178419179HCID 178419179, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under an argon atmosphere, to a solution of bis(4-dimethylamino-3,5-diisopropylphenyl)phosphine oxide (8.08 g, 18 mmoL) synthesized in Example 7 in toluene (48 mL) was added borane-tetrahydrofuran solution (60 mL, 3.3 equivalents) at 25° C. to 30° C. over 2 hr. Then, silica gel (7.0 g, 6.3 equivalents) was added to the mixture, and the mixture was stirred at room temperature for 1 hr. Then, silica gel was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was recrystallized from n-hexane to give the title compound (5.5 g, white crystals). yield 67%.

Workup

  1. additionThen, silica gel (7.0 g, 6.3 equivalents) was added to the mixture
  2. customThen, silica gel was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was recrystallized from n-hexane

Sources & evidence

ORD record
ord-43ba9b4636fd4a6f9595b784887c14e7
Source dataset
uspto-grants-2015_03
Patent number
US08981147B2

Reaction notes

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