Lithium hydroxide, monohydrate → (R)-1-[5-(3-chloro-phenyl)-isoxazol-3-yl]-ethanol

HRID 1453802Notes

Reaction equation

HRID 1453802 reaction equation
C([O:4][C@@H:5]([C:7]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[O:9][N:8]=1)[CH3:6])(=O)C.O.[OH-].[Li+]>C1COCC1.O>[Cl:18][C:14]1[CH:13]=[C:12]([C:10]2[O:9][N:8]=[C:7]([C@H:5]([OH:4])[CH3:6])[CH:11]=2)[CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 44605723(1R)-1-[5-(3-chlorophenyl)isoxazol-3-yl]ethyl acetate

Product 1

HCID 46701926(R)-1-[5-(3-chloro-phenyl)-isoxazol-3-yl]-ethanolYield 85%

Reagents, catalysts & solvents 1

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

Procedure

(1R)-1-[5-(3-chlorophenyl)isoxazol-3-yl]ethyl acetate (56 g, 211 mmol) and lithium hydroxide monohydrate (10.6 g, 253 mmol) were mixed with THF/Water (7/5, 1.2 L) and stirred at r.t. over night. Reducing the volume of the mixture in vacuo to about ½, followed by dilution with brine, extraction with ether and then drying over MgSO4 and in vacuo concentration gave crude product. The crude product was purified by flash column chromatography on silica using heptane/EtOAc=70:30, to give the title compound (40 g, 85%). 1H NMR: 7.73 (m, 1H), 7.63 (m, 1H), 7.38 (m, 2H), 6.57 (s, 1H), 5.07 (q, 1H), 2.44 (s, 1H), 1.59 (d, 3H).

Workup

  1. extractionfollowed by dilution with brine, extraction with ether
  2. dry with materialdrying over MgSO4 and in vacuo concentration
  3. customgave crude product
  4. customThe crude product was purified by flash column chromatography on silica

Sources & evidence

ORD record
ord-b97e1fb0d44e4c33a47251d88b95c6bf
Source dataset
uspto-grants-2009_01
Patent number
US07476684B2

Reaction notes

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