Lithium hydroxide, monohydrate → HCID 59457517, compound

HRID 1710741Notes

Reaction equation

HRID 1710741 reaction equation
O.[OH-].[Li+].[Cl:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][CH:17]=[C:18]([CH2:20][C:21]([O:23]C)=[O:22])[N:19]=2)=[CH:11][CH:10]=1>O.O1CCCC1>[Cl:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][CH:17]=[C:18]([CH2:20][C:21]([OH:23])=[O:22])[N:19]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59457469HCID 59457469, compound

Product 1

HCID 59457517HCID 59457517, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide hydrate (0.76 g, 18.11 mmol, 2 eq) in water (10 ml) is added to a solution of methyl {2-[4-(3-chloropropoxy)phenyl]-1,3-oxazol-4-yl}acetate ax62 (2.8 g, 9.06 mmol, 1 eq) in tetrahydrofuran (100 ml). The mixture is stirred at room temperature for 1 h. The mixture is then poured into water and extracted with diethyl ether (2×75 ml). The aqueous layer is acidified with 6 N aqueous hydrochloric acid and extracted with ethyl acetate. The organic layer is dried over magnesium sulfate and concentrated under vacuum to give 2.1 g of {2-[4-(3-chloropropoxy)phenyl]-1,3-oxazol-4-yl}acetic acid ax63 as a brown solid.

Workup

  1. extractionextracted with diethyl ether (2×75 ml)
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer is dried over magnesium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-fbde481e46044131846628cae6054b47
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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