Lithium hydroxide, monohydrate → HCID 67517033, compound

HRID 2173351Notes

Reaction equation

HRID 2173351 reaction equation
[N:1]1([C:6]2[CH:18]=[CH:17][C:9]3[CH:10]([C:13]([O:15]C)=[O:14])[CH2:11][O:12][C:8]=3[CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1.O[Li].O>CO.C1COCC1.O>[N:1]1([C:6]2[CH:18]=[CH:17][C:9]3[CH:10]([C:13]([OH:15])=[O:14])[CH2:11][O:12][C:8]=3[CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67518179HCID 67518179, compound

Product 1

HCID 67517033HCID 67517033, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of methyl 6-(1H-tetrazol-1-yl)-2,3-dihydro-1-benzofuran-3-carboxylate (3.3 g, 13.6 mmol) in 100 mL of MeOH/THF/H2O (2/2/1) was added LiOH.H2O (2.84 g, 67.5 mmol), and the mixture was stirred at ambient temperature overnight. 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 phases were washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue was re-crystallized from DCM to give 6-(1H-tetrazol-1-yl)-2,3-dihydro-1-benzofuran-3-carboxylic acid. 1H-NMR (300 MHz, DMSO) δ ppm 7.58 (d, J=7.8 Hz, 1H), 7.32-7.50 (m, 2H), 4.71-4.92 (m, 2H), 4.45-4.55 (m, 1H); MS m/z 233 (M+1)+.

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 phases were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was re-crystallized from DCM

Sources & evidence

ORD record
ord-ac8f90742e5642a69f3e123a07e61571
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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