Sodium Hydroxide → HCID 69841526, compound

HRID 1836624Notes

Reaction equation

HRID 1836624 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:8][C@H:7]1[C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([F:20])[CH:18]=2)[NH:13][CH:12]=1)=[O:10])=[O:5])C.[OH-].[Na+]>C(O)C>[F:20][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[C:9]([C@@H:7]1[CH2:8][C@H:6]1[C:4]([OH:5])=[O:3])=[O:10]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69840412HCID 69840412, compound

Product 1

HCID 69841526HCID 69841526, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The crude trans-2-(5-fluoro-3-indolylcarbonyl)cyclopropanecarboxylic acid ethyl ester (0.55 g, 2 mmol) was suspended in ethanol and sodium hydroxide solution (4 ml, 1N, 4 mmol) was added. The resultant solution was stirred for 4 hr at 20° and 0.5 hr at reflux. The ethanol was removed in vacuo and the residue mixed with water. The mixture was extracted with ethyl acetate. The aqueous layer was separated and made acidic with 12 N HCl. The precipitate was collected and air dried to give trans-2-(5-fluoro-3-indolylcarbonyl)cyclopropanecarboxylic acid as an off-white solid (0.30 g), mp 276-277 dec. LC/MS mw=247; retention time 1.19 min. Mol wt calc1d for C13H10F NO2: 247.

Workup

  1. temperatureat reflux
  2. customThe ethanol was removed in vacuo
  3. additionthe residue mixed with water
  4. extractionThe mixture was extracted with ethyl acetate
  5. customThe aqueous layer was separated
  6. customThe precipitate was collected
  7. customair dried

Sources & evidence

ORD record
ord-fff52ab1810e412b95bb687ff4e5dc97
Source dataset
uspto-grants-2004_08
Patent number
US06777437B2

Reaction notes

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