Borane;tetrahydrofuran → HCID 178419177, compound

HRID 2361553Notes

Reaction equation

HRID 2361553 reaction equation
[CH3:1][N:2]([CH3:28])[C:3]1[C:8]([CH2:9][CH3:10])=[CH:7][C:6]([PH:11](=O)[C:12]2[CH:17]=[C:16]([CH2:18][CH3:19])[C:15]([N:20]([CH3:22])[CH3:21])=[C:14]([CH2:23][CH3:24])[CH:13]=2)=[CH:5][C:4]=1[CH2:26][CH3:27].[BH3:29].O1CCCC1>C1(C)C=CC=CC=1>[CH3:28][N:2]([CH3:1])[C:3]1[C:8]([CH2:9][CH3:10])=[CH:7][C:6]([PH:11][C:12]2[CH:17]=[C:16]([CH2:18][CH3:19])[C:15]([N:20]([CH3:21])[CH3:22])=[C:14]([CH2:23][CH3:24])[CH:13]=2)=[CH:5][C:4]=1[CH2:26][CH3:27].[BH3:29]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 178436979HCID 178436979, compound

Product 1

HCID 178419177HCID 178419177, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under an argon atmosphere, to a solution of bis(4-dimethylamino-3,5-diethylphenyl)phosphine oxide (8.12 g, 20 mmoL) synthesized in Example 4 in toluene (48 mL) was added borane-tetrahydrofuran solution (68 mL, 3.5 equivalents) at 25° C. to 30° C. over 2 hr. Then, silica gel (8.3 g, 7.0 equivalents) was added to the mixture, and the mixture was stirred at room temperature for 1 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 50 g, toluene) to give the title compound (5.1 g, colorless oil). yield 64%.

Workup

  1. additionThen, silica gel (8.3 g, 7.0 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 50 g, toluene)

Sources & evidence

ORD record
ord-41cc354dab554dc789bedde41055643c
Source dataset
uspto-grants-2014_04
Patent number
US08691718B2

Reaction notes

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