HCID 18677117, compound → HCID 18677134, compound

HRID 1634096Notes

Reaction equation

HRID 1634096 reaction equation
[CH3:1][C:2]([O-])([CH3:4])[CH3:3].[K+].[N+:7]([C:10]1[CH:15]=[CH:14][C:13]([N:16]2[C:20]([CH2:21][CH3:22])=[CH:19]C(C(=O)C)=[N:17]2)=[CH:12][CH:11]=1)([O-:9])=[O:8]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[N+:7]([C:10]1[CH:11]=[CH:12][C:13]([N:16]2[C:20]([CH2:21][CH3:22])=[CH:19][C:1]([C:2]([CH3:4])=[CH2:3])=[N:17]2)=[CH:14][CH:15]=1)([O-:9])=[O:8]

Participants

5

Reactant 2

HCID 18677117HCID 18677117, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18677134HCID 18677134, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl triphenylphosphonium bromide (3.47 g, 9.72 mmol) in THF (20 mL) was added 1 M KOt-Bu in THF (9.73 mL, 9.73 mmol) followed by the above ketone (2.10 g, 8.10 mmol). The mixture was stirred at room temperature for 4 hrs, quenched with water and extracted with ethyl acetate. The extract was dried over Na2SO4 and concentrated. The residue was slurried with hexane and filtered. The filtrate was concentrated to give the title compound as a white solid (1.46 g, 70%). mp: 61-63° C.

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over Na2SO4
  4. concentrationconcentrated
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-7ee510557bf844379b6e9150ca313acd
Source dataset
uspto-grants-2003_01
Patent number
US06506747B1

Reaction notes

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