Phosphanium bromide → HCID 178438821, compound

HRID 486497Notes

Reaction equation

HRID 486497 reaction equation
[CH2:1]([Li])CCC.[Br-].[PH4+].[C:8]([C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16]([CH2:21][CH2:22][CH2:23][CH3:24])=[N:15][C:14]2=[O:25])(=O)[CH3:9]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[CH2:21]([C:16]1[NH:17][C:18]2[C:13]([C:14](=[O:25])[N:15]=1)=[CH:12][C:11]([C:8]([CH3:1])=[CH2:9])=[CH:20][CH:19]=2)[CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 3

HCID 21868956Phosphanium bromideHCID 178418339ButyllithiumHCID 178441846HCID 178441846, compound

Product 1

HCID 178438821HCID 178438821, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a suspension of 3.66 g of methyltriphenylphosphonium bromide in 30 ml of dry tetrahydrofuran, cooled to -78° C., is added dropwise 5.9 ml of a 1.73M solution of n-butyllithium in hexanes. Following complete addition, the reaction mixture is allowed to warm to room temperature and stirred for 15 minutes, until all the phosphonium bromide is dissolved. The reaction mixture is then recooled to -78° C. and a suspension of 6-acetyl-2-butyl-4(1H)-quinazolinone in 15 ml of dry tetrahydrofuran is added. The reaction is allowed to warm to room temperature and stirred for 24 hours followed by quenching with saturated ammonium chloride solution. After diluting with 10 ml of water, the aqueous layer is extracted with chloroform and the combined organics dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified by flash chromatography on silica gel, eluting with 1:2 ethyl acetate-hexanes to give 0.23 g of the desired product as a white solid.

Workup

  1. additionaddition
  2. temperatureto warm to room temperature
  3. dissolutionis dissolved
  4. customis then recooled to -78° C.
  5. additionis added
  6. temperatureto warm to room temperature
  7. customby quenching with saturated ammonium chloride solution
  8. additionAfter diluting with 10 ml of water
  9. extractionthe aqueous layer is extracted with chloroform
  10. dry with materialthe combined organics dried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customThe residue is purified by flash chromatography on silica gel
  14. washeluting with 1:2 ethyl acetate-hexanes

Sources & evidence

ORD record
ord-8ed55d49f666477ba4dae468563bd85b
Source dataset
uspto-grants-1994_03
Patent number
US05292734

Reaction notes

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