Lithium hydroxide, monohydrate → HCID 67517234, compound

HRID 2173275Notes

Reaction equation

HRID 2173275 reaction equation
[F:1][C:2]1[C:3]([I:17])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([C:12]([O:14]CC)=[O:13])[O:7][CH2:6][CH2:5]2.O[Li].O>CO.C1COCC1.O>[F:1][C:2]1[C:3]([I:17])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([C:12]([OH:14])=[O:13])[O:7][CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67517908HCID 67517908, compound

Product 1

HCID 67517234HCID 67517234, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of ethyl 6-fluoro-5-iodo-3,4-dihydro-1H-isochromene-1-carboxylate (1.6 g, 4.5 mmol) in 25 mL of MeOH/THF/H2O (2/2/1) was added LiOH.H2O (700 mg, 18.3 mmol), and the mixture was stirred at ambient temperature for 30 min. The solvents were removed under vacuum, and the residue was added 50 mL of water and extracted with ether. The aqueous layer was then acidified with 4 N HCl to pH=3 in ice bath, and extracted with EtOAc. The combined organic phase was washed with brine, dried over anhydrous sodium sulfate and concentrated to afford 6-fluoro-5-iodo-3,4-dihydro-1H-isochromene-1-carboxylic acid.

Workup

  1. customThe solvents were removed under vacuum
  2. additionthe residue was added 50 mL of water
  3. extractionextracted with ether
  4. extractionextracted with EtOAc
  5. washThe combined organic phase was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e6dc212fdf2d45a99f45c02a7661ed01
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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