Acetone cardice → HCID 22388180, compound

HRID 1072787Notes

Reaction equation

HRID 1072787 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([C:16]3[O:17][CH2:18][C:19]([CH3:22])([CH3:21])[N:20]=3)=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]1[P:23]([O:27][CH3:28])([O:25][CH3:26])=[O:24])=[O:5])[CH3:2].CCCCCC.C([Li])CCC.C(=O)=O.CC(C)=O.I[CH2:48][C:49]1[CH:54]=[CH:53][C:52]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)=[CH:51][CH:50]=1>C1COCC1.O>[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([C:16]3[O:17][CH2:18][C:19]([CH3:21])([CH3:22])[N:20]=3)=[CH:13][CH:14]=2)[C:9]([CH2:48][C:49]2[CH:54]=[CH:53][C:52]([C:55]3[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=3)=[CH:51][CH:50]=2)=[CH:8][CH:7]1[P:23]([O:25][CH3:26])([O:27][CH3:28])=[O:24])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 18522661Acetone cardice2×HCID 219099744-(Iodomethyl)biphenylHCID 22388237HCID 22388237, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 22388180HCID 22388180, compoundYield 56.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-Ethoxycarbonyl-6-(4,5-dihydro-4,4-dimethyloxazol-2-yl)-2-dimethoxyphosphoryl-1,2-dihydroquinoline (934 mg) was dissolved in THF (10 ml), and a 1.6 M n-butyllithiumhexane solution (1.8 ml) was added under cooling with dry ice-acetone. The mixture was stirred for 1 hr at the same temperature. 4-(Iodomethyl)biphenyl (740 mg, 2.52 mmol) was added under cooling with dry ice-acetone, and the mixture was stirred at −20° C. for 1 hr and at 0° C. for 1 hr. Then, water was added, and the mixture was stirred for 0.5 hr at room temperature and extracted three times with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated to dryness under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate, ethyl acetate/methanol=20/1) to give the objective compound (738 mg) as a yellow powder.

Workup

  1. stirringthe mixture was stirred at −20° C. for 1 hr and at 0° C. for 1 hr
  2. stirringthe mixture was stirred for 0.5 hr at room temperature
  3. extractionextracted three times with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate, ethyl acetate/methanol=20/1)

Sources & evidence

ORD record
ord-23fbf08b273941c9874c1e0964b65e21
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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