Sodium Hydroxide → HCID 59117356, compound

HRID 2227984Notes

Reaction equation

HRID 2227984 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:20][N:21]2[CH:25]=[CH:24][N:23]=[CH:22]2)=[CH:9][C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([O:15]C)=[O:14])=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[CH2:20][N:21]2[CH:25]=[CH:24][N:23]=[CH:22]2)=[CH:9]\[C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([OH:15])=[O:14])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54470991HCID 54470991, compound

Product 1

HCID 59117356HCID 59117356, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the product from step B (E and Z isomers) (11 g , 32.7 mmol) in MeOH (150 ml) was treated with 2N NaOH (32 ml, 65 mmol) for 3 hours. Methanol was then evaporated and the solution was acidified to pH 5.5 with 6N HCl. The resulting precipitate was filtered and washed with a small quantity of water. The precipitate was taken up in MeOH. The insoluble material was washed with a mixture of MeOH/ether to give after drying 2.3 g of E isomer 3-((E)-2-(4-fluorophenyl)-3-(imidazol-1-yl)-prop-1-enyl)benzoic acid (22%). The above filtrate was evaporated and triturated in ether to give the E isomer 3-((E)-2-(4-fluorophenyl)-3-(imidazol-1-yl)-prop-1-enyl)benzoic acid (7.7 g, 67%) as a solid.

Workup

  1. customMethanol was then evaporated
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with a small quantity of water
  4. washThe insoluble material was washed with a mixture of MeOH/ether
  5. customto give
  6. dry with materialafter drying 2.3 g of E isomer 3-((E)-2-(4-fluorophenyl)-3-(imidazol-1-yl)-prop-1-enyl)benzoic acid (22%)
  7. customThe above filtrate was evaporated
  8. customtriturated in ether

Sources & evidence

ORD record
ord-bfdea2cddb214c30a66981cd66525d74
Source dataset
uspto-grants-2002_07
Patent number
US06414145B1

Reaction notes

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