Borane;tetrahydrofuran → HCID 178419179, compound

HRID 2361555Notes

Reaction equation

HRID 2361555 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-eb658a9e49ce4159984f9847c2e957ea
Source dataset
uspto-grants-2014_04
Patent number
US08691718B2

Reaction notes

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