18-Crown-6 → methyl 4-[(Z)-3-(imidazol-1-yl)-2-(thiazol-2-yl)-prop-1-enyl]-2-phenyl-benzoate

HRID 2227994Notes

Reaction equation

HRID 2227994 reaction equation
[N:1]1([CH2:6][C:7]([C:9]2[S:10][CH:11]=[CH:12][N:13]=2)=O)[CH:5]=[CH:4][N:3]=[CH:2]1.[Br-].[CH3:15][O:16][C:17]([C:19]1[CH:44]=[CH:43][C:22]([CH2:23][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:21][C:20]=1[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:18].C1OCCOCCOCCOCCOCCOC1.CC(C)([O-])C.[K+]>C(Cl)Cl>[N:1]1([CH2:6]/[C:7](/[C:9]2[S:10][CH:11]=[CH:12][N:13]=2)=[CH:23]/[C:22]2[CH:43]=[CH:44][C:19]([C:17]([O:16][CH3:15])=[O:18])=[C:20]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[CH:21]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 2855718-Crown-6HCID 223249842-(Imidazol-1-yl)-1-(thiazol-2-yl)-ethanoneHCID 23665647Potassium tert-butoxideHCID 865903334-Methyloxycarbonyl-3-phenyl-benyl-triphenylphosphonium bromide

Product 1

HCID 70030731methyl 4-[(Z)-3-(imidazol-1-yl)-2-(thiazol-2-yl)-prop-1-enyl]-2-phenyl-benzoateYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-(imidazol-1-yl)-1-(thiazol-2-yl)ethanone (1.66 g; 8.5 mmol), 4-methyloxycarbonyl-3-phenyl-benzyl-triphenylphosphonium bromide (see Example 7, compound a), step E), (7.3 g; 12.8 mmol) and 18-crown-6 (0.1 g; 0.37 mmol) in methylene chloride (60 ml) was added at −50° C., under argon atmosphere, potassium tert-butoxide (1.56 g; 12.8 mmol). After 20 min at −50° C., the mixture was stirred at room temperature for 4 hours. The solvent was evaporated to dryness and the residue purified on HP20SS resin eluting with a gradient of 0-60% CH3CN/(NH4)2CO3 buffer (2 g/l pH 6.8) to give methyl 4-[(Z)-3-(imidazol-1-yl)-2-(thiazol-2-yl)-prop-1-enyl]-2-phenyl-benzoate (1.1 g; 72%).

Workup

  1. additionwas added at −50° C., under argon atmosphere
  2. customThe solvent was evaporated to dryness
  3. customthe residue purified on HP20SS resin
  4. washeluting with a gradient of 0-60% CH3CN/(NH4)2CO3 buffer (2 g/l pH 6.8)

Sources & evidence

ORD record
ord-c616a3ecd33440538906f9ad34b13f3d
Source dataset
uspto-grants-2002_07
Patent number
US06414145B1

Reaction notes

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