Methanol → 3,3-Bis(4-fluorophenyl)-2-[1-(1-methylethyl)-1H-tetrazol-5-yl]-2-propenoic acid

HRID 974455Notes

Reaction equation

HRID 974455 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[C:9]([C:15]2[N:19]([CH:20]([CH3:22])[CH3:21])[N:18]=[N:17][N:16]=2)[C:10]([O:12]CC)=[O:11])=[CH:4][CH:3]=1.O1CCCC1.CO.[Li+].[OH-]>OS(O)(=O)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[C:9]([C:15]2[N:19]([CH:20]([CH3:22])[CH3:21])[N:18]=[N:17][N:16]=2)[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 14723869ethyl 3,3-bis(4-fluorophenyl)-2-[1-(1-methylethyl)-1H-tetrazol-5-yl]-2-propenoate

Product 1

HCID 147238703,3-Bis(4-fluorophenyl)-2-[1-(1-methylethyl)-1H-tetrazol-5-yl]-2-propenoic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a chilled (0° C.) solution of ethyl 3,3-bis(4-fluorophenyl)-2-[1-(1-methylethyl)-1H-tetrazol-5-yl]-2-propenoate (0.95 g, 2.39 mmoles) in 20 mL of 1:1 (v/v) mixture of tetrahydrofuran and methanol was added an aqueous solution of LiOH (4.0 mL, 3 Molar) in one single portion. The reaction mixture was stirred at 0° C. for 15 minutes followed by warming up to ambient temperature. Saponification was allowed to proceed at room temperature for four hours forming a very pale clear solution. The crude reaction mixture was diluted with 12 mL of 2M H2SO4 and the product was extracted into diethyl ether (40 mL×2). The organic layers were combined, dried over MgSO4, concentrated under reduced pressure and then vigorously dried under high vacuum (0.01 mmHg) at room temperature for 24 hours to yield the title compound. The propenoic acid was then utilized in the next step without further purification.

Workup

  1. temperatureby warming up to ambient temperature
  2. waitto proceed at room temperature for four hours
  3. customforming a very pale clear solution
  4. customThe crude reaction mixture
  5. extractionthe product was extracted into diethyl ether (40 mL×2)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customvigorously dried under high vacuum (0.01 mmHg) at room temperature for 24 hours

Sources & evidence

ORD record
ord-c3f9681473e54b3096c63b03353bd012
Source dataset
uspto-grants-1991_11
Patent number
US05068346

Reaction notes

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