(3-Benzyloxypropyl)triphenylphosphonium bromide → 2-[6-(-Benzyloxy-but-1-enyl)-benzoimidazol-1-yl]-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid ethyl ester

HRID 1667762Notes

Reaction equation

HRID 1667762 reaction equation
[Br-].[CH2:2]([O:9][CH2:10][CH2:11][CH2:12][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1([Li])C=CC=CC=1.[CH2:39]([O:41][C:42]([C:44]1[S:48][C:47]([N:49]2[C:53]3[CH:54]=[C:55]([CH:58]=O)[CH:56]=[CH:57][C:52]=3[N:51]=[CH:50]2)=[N:46][C:45]=1[C:60]1[CH:65]=[CH:64][CH:63]=[C:62]([Cl:66])[CH:61]=1)=[O:43])[CH3:40]>O1CCCC1>[CH2:39]([O:41][C:42]([C:44]1[S:48][C:47]([N:49]2[C:53]3[CH:54]=[C:55]([CH:58]=[CH:12][CH2:11][CH2:10][O:9][CH2:2][C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH:56]=[CH:57][C:52]=3[N:51]=[CH:50]2)=[N:46][C:45]=1[C:60]1[CH:65]=[CH:64][CH:63]=[C:62]([Cl:66])[CH:61]=1)=[O:43])[CH3:40]

Participants

5

Reactant 3

HCID 10929077(3-Benzyloxypropyl)triphenylphosphonium bromideHCID 866428374-(3-Chloro-phenyl)-2-(6-formyl-benzoimidazol-1-yl)-thiazole-5-carboxylic acid ethyl esterHCID 178506676HCID 178506676, compound

Product 1

HCID 674446332-[6-(-Benzyloxy-but-1-enyl)-benzoimidazol-1-yl]-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid ethyl esterYield 52.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 0.983 g (2 mmole) of (3-benzyloxypropyl)triphenylphosphonium bromide and 20 mL of tetrahydrofuran at −78 degrees was added 1.33 mL (2.4 mmole) of 1.8 M phenyllithium solution. The mixture was stirred for 10 minutes and then 0.823 g (2 mmole) of 4-(3-chloro-phenyl)-2-(6-formyl-benzoimidazol-1-yl)-thiazole-5-carboxylic acid ethyl ester (I.41a) was added. The reaction was allowed to warm up to room temperature, stirred for 2 hours and then quenched by the addition of 10 mL of saturated ammonium chloride solution. The layers were separated. The aqueous layer was extracted twice with 20 mL of ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with methanol-dichloromethane (gradient 0:100-1.5:98.5) to give 0.568 g of 2-[6-(-benzyloxy-but-1-enyl)-benzoimidazol-1-yl]-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid ethyl ester (I.41b) as a yellow solid.

Workup

  1. stirringstirred for 2 hours
  2. customquenched by the addition of 10 mL of saturated ammonium chloride solution
  3. customThe layers were separated
  4. extractionThe aqueous layer was extracted twice with 20 mL of ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel chromatography
  10. washeluting with methanol-dichloromethane (gradient 0:100-1.5:98.5)

Sources & evidence

ORD record
ord-c76dca8f823d4e2a8ac6aad2199cf725
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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