((7-Chloroquinolin-2-yl)methyl)triphenylphosphonium bromide → Methyl 3-((1-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(2-hydroxy-2-propyl)phenyl)propyl)thio)-2-methylpropanoate

HRID 865457Notes

Reaction equation

HRID 865457 reaction equation
[Br-].[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([CH2:13][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[N:10]2)=[CH:5][CH:4]=1.[Li]CCCC.[CH:38]([C:40]1[CH:41]=[C:42]([CH:46]([S:59][CH2:60][CH:61]([CH3:66])[C:62]([O:64][CH3:65])=[O:63])[CH2:47][CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=2[C:55]([OH:58])([CH3:57])[CH3:56])[CH:43]=[CH:44][CH:45]=1)=O>C1COCC1>[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([CH:13]=[CH:38][C:40]3[CH:41]=[C:42]([CH:46]([S:59][CH2:60][CH:61]([CH3:66])[C:62]([O:64][CH3:65])=[O:63])[CH2:47][CH2:48][C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=4[C:55]([OH:58])([CH3:57])[CH3:56])[CH:43]=[CH:44][CH:45]=3)=[N:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 10391903((7-Chloroquinolin-2-yl)methyl)triphenylphosphonium bromideHCID 53988090Methyl 3-((1-(3-formylphenyl)-3-(2-(2-hydroxy-2-propyl)phenyl)propyl)thio)-2-methylpropanoateHCID 178418339Butyllithium

Product 1

HCID 54569616Methyl 3-((1-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(2-hydroxy-2-propyl)phenyl)propyl)thio)-2-methylpropanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To ((7-chloro-2-quinolinyl)methyl)triphenylphosphonium bromide (525 mg, 1.01 mmol, U.S. Pat. No. 4,851,409, Example 4, Step 2) in a THF (2 mL) solution at -78° C. was added dropwise 1.6M nBuLi (472 mL, 0.945 mmol). After a few minutes, the aldehyde of Step 11 (140 mg, 0.338 mmol) was then added and the resulting mixture was stirred at -78° C. for 30 min. The reaction mixture was then allowed to warm to r.t. for 30 min and was quenched by the addition of 25% aq NH4OAc. The title product was then extracted with EtOAc, dried on Na2SO4 and evaporated under reduced pressure. After purification by flash chromatography (20% EtOAc in toluene), the title compound was obtained as an oil (170 mg, 89%).

Workup

  1. waitAfter a few minutes
  2. temperatureto warm to r.t. for 30 min
  3. customwas quenched by the addition of 25% aq NH4OAc
  4. extractionThe title product was then extracted with EtOAc
  5. customdried on Na2SO4
  6. customevaporated under reduced pressure
  7. customAfter purification by flash chromatography (20% EtOAc in toluene)

Sources & evidence

ORD record
ord-c185780d724949f3a399162d641d6bbe
Source dataset
uspto-grants-1996_10
Patent number
US05565473

Reaction notes

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