Carbon Dioxide → HCID 70298268, compound

HRID 1421849Notes

Reaction equation

HRID 1421849 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]2[CH:6]([CH3:9])[NH:7][O:8][C:4]=2[CH:3]=1.C([Li])CCC.[C:17](=[O:19])=[O:18].O>C1COCC1>[F:1][C:2]1[CH:11]=[CH:10][C:5]2[CH:6]([CH3:9])[NH:7][O:8][C:4]=2[C:3]=1[C:17]([OH:19])=[O:18]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 962WaterHCID 70298582HCID 70298582, compoundHCID 178418339Butyllithium

Product 1

HCID 70298268HCID 70298268, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 6-fluoro-3-methyl-1,2(2H)-benzisoxazole (5.5 g, 0.037 mole) in THF (100 mL) was cooled in a dry ice-acetone bath, and 2.5 M n-butyllithium in hexanes (16 mL, 0.040 mole) was added dropwise. Upon completion of addition, the reaction mixture was stirred for one hour. The reaction mixture was then exposed to a CO2 atmosphere where it stirred for three hours. After this time, the reaction mixture was poured into water. The mixture was washed with ether, acidified with hydrochloric acid, and then extracted repeatedly with ether. The combine extracts were washed with water, dried with magnesium sulfate and concentrated yielding 4.5 grams of [6-fluoro-3-methyl-1,2(2H)-benzisoxazol-7-yl]carboxylic acid. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. stirringstirred for three hours
  3. washThe mixture was washed with ether
  4. extractionextracted repeatedly with ether
  5. washThe combine extracts were washed with water
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-60f7c635a89048deb96efb7395df181f
Source dataset
uspto-grants-2000_06
Patent number
US06080702

Reaction notes

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