[4-[5-[4-(2-Methylpropyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methanol → (+/-)-4-(5-(4-(2-Methylpropyl)phenyl)-1,2,4-oxadiazol-3-yl)-1-(1-hydroxyethyl)benzene

HRID 1268934Notes

Reaction equation

HRID 1268934 reaction equation
[CH3:1][CH:2]([CH3:23])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][CH:16]=3)[N:11]=2)=[CH:6][CH:5]=1.[CH3:24][Mg]I>C1COCC1>[CH3:1][CH:2]([CH3:23])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:16]=[CH:17][C:18]([CH:21]([OH:22])[CH3:24])=[CH:19][CH:20]=3)[N:11]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 11645224[4-[5-[4-(2-Methylpropyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methanolHCID 178418373HCID 178418373, compound

Product 1

HCID 18446989(+/-)-4-(5-(4-(2-Methylpropyl)phenyl)-1,2,4-oxadiazol-3-yl)-1-(1-hydroxyethyl)benzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.5 g (1.63 mmol) of Aldehyde 1 in 10 mL of THF was treated with 1.1 mL (3.3 mmol) of methylmagnesium iodide (3.0 M in diethyl ether) at −78° C. and was allowed to warm to rt over 30 min. The resulting mixture was quenched with 5 mL of 1 N HCl and was extracted with 30 mL of ethyl acetate. The extract was washed, dried and concentrated to afford the title compound: ESI-MS 323 (M+H); LC-1: 4.2 min.

Workup

  1. customThe resulting mixture was quenched with 5 mL of 1 N HCl
  2. extractionwas extracted with 30 mL of ethyl acetate
  3. washThe extract was washed
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1bd5d4245cc949ee88fc2d67f64ae302
Source dataset
uspto-grants-2007_04
Patent number
US07199142B2

Reaction notes

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