Tetrahydrofuran → {4-[3-(4-Isobutylphenyl)-1,2,4-oxadiazol-5-yl]phenyl}methanol

HRID 2242228Notes

Reaction equation

HRID 2242228 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[OH:19][CH2:20][C:21]1[CH:42]=[CH:41][C:24]([C:25]([O:27][N:28]=[C:29]([C:31]2[CH:36]=[CH:35][C:34]([CH2:37][CH:38]([CH3:40])[CH3:39])=[CH:33][CH:32]=2)[NH2:30])=O)=[CH:23][CH:22]=1.C1COCC1>C(OCC)(=O)C>[CH2:37]([C:34]1[CH:35]=[CH:36][C:31]([C:29]2[N:30]=[C:25]([C:24]3[CH:41]=[CH:42][C:21]([CH2:20][OH:19])=[CH:22][CH:23]=3)[O:27][N:28]=2)=[CH:32][CH:33]=1)[CH:38]([CH3:40])[CH3:39]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 72530370N'-{[4-(Hydroxymethyl)benzoyl]oxy}-4-isobutylbenzenecarboximidamide

Product 1

HCID 59204309{4-[3-(4-Isobutylphenyl)-1,2,4-oxadiazol-5-yl]phenyl}methanolYield 46%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Tetrabutylammonium fluoride (1.0 M solution in THF, 10 mL) was added to a solution of N′-{[4-(hydroxymethyl)benzoyl]oxy}-4-isobutylbenzenecarboximidamide (3.07 g, 9.42 mmol) and THF (50 mL) and stirred at room temperature for 20 hours. The reaction mixture was diluted with ethyl acetate, washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo to give the title compound (1.33 g, 46% yield) as a crude solid.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-97fc3b451b06416d830a757cdf6a8469
Source dataset
uspto-grants-2010_03
Patent number
US07671043B2

Reaction notes

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