Borane;tetrahydrofuran → HCID 178419190, compound

HRID 875287Notes

Reaction equation

HRID 875287 reaction equation
[CH2:1]([N:3]([CH2:23][CH3:24])[C:4]1[CH:9]=[CH:8][C:7]([PH:10](=O)[C:11]2[CH:16]=[CH:15][C:14]([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:13][CH:12]=2)=[CH:6][CH:5]=1)[CH3:2].[BH3:25].O1CCCC1>O1CCCC1>[CH2:20]([N:17]([CH2:18][CH3:19])[C:14]1[CH:13]=[CH:12][C:11]([PH:10][C:7]2[CH:8]=[CH:9][C:4]([N:3]([CH2:23][CH3:24])[CH2:1][CH3:2])=[CH:5][CH:6]=2)=[CH:16][CH:15]=1)[CH3:21].[BH3:25]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 178463848HCID 178463848, compound

Product 1

HCID 178419190HCID 178419190, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen stream, to a solution of bis(4-diethylaminophenyl)phosphine oxide (3.76 g, 10 mmoL) synthesized in Example 10 in tetrahydrofuran (35 mL) was added borane-tetrahydrofuran solution (35 mL, 3.3 equivalents) at 25° C. to 30° C. over 2 hr. Then, silica gel (6.3 g, 9.7 equivalents) was added to the mixture, and the mixture was stirred at room temperature for 3 hr. Then, silica gel was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was recrystallized from n-hexane/ethyl acetate (1/1) to give the title compound (1.8 g, white crystals). yield 49%. melting point 108.5° C.

Workup

  1. additionThen, silica gel (6.3 g, 9.7 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/ethyl acetate (1/1)

Sources & evidence

ORD record
ord-2785e53fc756407ea5e31be53db4ed8e
Source dataset
uspto-grants-2015_03
Patent number
US08981147B2

Reaction notes

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