Lithium hydroxide, monohydrate → (+)-(1R)-1-[5-(3-chlorophenyl)-[1,2,4]oxadiazol-3-yl]ethanol

HRID 732117Notes

Reaction equation

HRID 732117 reaction equation
C([O:4][C@@H:5]([C:7]1[N: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])[N:11]=2)[CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 57837970(+)-(1R)-1-[5-(3-chlorophenyl)-[1,2,4]oxadiazol-3-yl]ethyl acetate

Product 1

HCID 57837962(+)-(1R)-1-[5-(3-chlorophenyl)-[1,2,4]oxadiazol-3-yl]ethanolYield 97%

Reagents, catalysts & solvents 1

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

Procedure

7.13 g (26.7 mmol) (+)-(1R)-1-[5-(3-chlorophenyl)-[1,2,4]oxadiazol-3-yl]ethyl acetate and 2.33 g (56.7 mmol) lithium hydroxide monohydrate were mixed with 1:1 THF/Water (100 mL) and stirred for 18 h. Reducing the volume of the mixture in vacuo to about ½, followed by dilution with brine and extraction with ethyl acetate. 5.8 g (97%) of the title compound was obtained after evaporation and drying. 1H NMR: 8.14 (s, 1 H), 8.02 (d, 1 H), 7.57 (d, 1 H), 7.47 (t, 1 H), 5.04-5.14 (m, 1 H), 2.42 (br s, 1 H), 1.67 (d, 3 H)

Workup

  1. extractionfollowed by dilution with brine and extraction with ethyl acetate

Sources & evidence

ORD record
ord-508d2038566446659252a801c9103d97
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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