Lithium hydroxide, monohydrate → (1R)-1-[2-(3-Methylphenyl)-2H-tetrazol-5-yl]ethanol

HRID 2422730Notes

Reaction equation

HRID 2422730 reaction equation
O.[OH-].[Li+].C([O:7][C@@H:8]([C:10]1[N:11]=[N:12][N:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=2)[N:14]=1)[CH3:9])(=O)C>O1CCCC1.O>[CH3:21][C:17]1[CH:16]=[C:15]([N:13]2[N:12]=[N:11][C:10]([C@H:8]([OH:7])[CH3:9])=[N:14]2)[CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 25264100(1R)-1-[2-(3-Methylphenyl)-2H-tetrazol-5-yl]ethyl acetate

Product 1

HCID 25265528(1R)-1-[2-(3-Methylphenyl)-2H-tetrazol-5-yl]ethanolYield 99%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Lithium hydroxide monohydrate (16.68 g, 400 mmol) was added to a stirred solution of (1R)-1-[2-(3-methylphenyl)-2H-tetrazol-5-yl]ethyl acetate (46.6 g, 190 mmol) in tetrahydrofuran/water (1:1, 750 mL). After 3 hour reaction time the mixture was concentrated to half volume. Brine (100 mL) was added and the mixture was extracted with ethyl acetate (3×100 mL). The combined organic layer was dried over sodium sulfate, filtered and concentrated to give the title product (38.18 g, 99%).

Workup

  1. customAfter 3 hour reaction time the mixture
  2. concentrationwas concentrated to half volume
  3. additionBrine (100 mL) was added
  4. extractionthe mixture was extracted with ethyl acetate (3×100 mL)
  5. dry with materialThe combined organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-aea7c995e88f4370af90f57d8b693afd
Source dataset
uspto-grants-2011_06
Patent number
US07960422B2

Reaction notes

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