Carbon Dioxide → 4-[2-(4-Pentyloxyphenyl)thiazol-5-yl]benzoic acid

HRID 2270048Notes

Reaction equation

HRID 2270048 reaction equation
[CH2:1]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]([C:18]3[CH:23]=[CH:22][C:21](Br)=[CH:20][CH:19]=3)=[CH:16][N:17]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].C([Li])CCC.[C:30](=[O:32])=[O:31].Cl>O1CCCC1.O>[CH2:1]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]([C:18]3[CH:23]=[CH:22][C:21]([C:30]([OH:32])=[O:31])=[CH:20][CH:19]=3)=[CH:16][N:17]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 183310882-(4-Pentyloxyphenyl)-5-(4-bromophenyl)thiazoleHCID 178418339Butyllithium2×

Product 1

HCID 183310784-[2-(4-Pentyloxyphenyl)thiazol-5-yl]benzoic acidYield 80.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-60 °C

Procedure

A solution of 2-(4-pentyloxyphenyl)-5-(4-bromophenyl)thiazole (2.3 g) in dry tetrahydrofuran (60 ml) was cooled to −60° C., and a solution of n-butyllithium (1.66M in n-hexane, 4.46 ml) was added slowly to maintain the reaction temperature at −60° C. After stirring for 1 hour, a solution of n-butyllithium (1.66M in n-hexane, 1.0 ml) was additionally added. The reaction mixture was allowed to warm to −40° C. After stirring for 30 minutes, dry-ice (5 g) was added. The reaction mixture was allowed to warm to room temperature over 30 minutes. To the reaction mixture was added water (25 ml) and 0.5N-hydrochloric acid (100 ml), then extracted with dichloromethane (500 ml). The organic layer was washed with brine, and dried over magnesium sulfate. Magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure. The solids were slurried in acetonitrile, and collected by filtration to give 4-[2-(4-pentyloxyphenyl)thiazol-5-yl]benzoic acid (1.70 g).

Workup

  1. temperatureto warm to −40° C
  2. stirringAfter stirring for 30 minutes
  3. temperatureto warm to room temperature over 30 minutes
  4. extractionextracted with dichloromethane (500 ml)
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationMagnesium sulfate was filtered off
  8. customthe filtrate was evaporated under reduced pressure
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-0beaf393016e48568e4f7a6a5ec84e9d
Source dataset
uspto-grants-2001_12
Patent number
US06331521B1

Reaction notes

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