Hydrochloric Acid → (4-(5-Ethyl-1,3,4-oxadiazol-2-yl)phenyl)methanol

HRID 512617Notes

Reaction equation

HRID 512617 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[O:17][C:18]([CH2:21][CH3:22])=[N:19][N:20]=2)=[CH:12][CH:11]=1)(C(C)(C)C)(C)C.Cl>CO>[CH2:21]([C:18]1[O:17][C:16]([C:13]2[CH:14]=[CH:15][C:10]([CH2:9][OH:8])=[CH:11][CH:12]=2)=[N:20][N:19]=1)[CH3:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 584319792-(4-(((Tert-butyldimethylsilyl)oxy)methyl)phenyl)-5-ethyl-1,3,4-oxadiazole

Product 1

HCID 58432072(4-(5-Ethyl-1,3,4-oxadiazol-2-yl)phenyl)methanolYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an ice-cold solution of 2-(4-(((tert-butyldimethylsilyl)oxy)methyl)phenyl)-5-ethyl-1,3,4-oxadiazole (3.0 g, 9.4 mmol) in MeOH (30 mL) was added 1 M HCl (20 mL, 20 mmol) dropwise. The reaction was stirred over ice for 1 hr then concentrated. The residue was quenched with saturated aqueous NaHCO3 and extracted with EtOAc. The combined organics were dried over Na2SO4 and concentrated in vacuo to give (4-(5-ethyl-1,3,4-oxadiazol-2-yl)phenyl)methanol as an off-white solid (1.92 g, 93% yield).

Workup

  1. concentrationthen concentrated
  2. customThe residue was quenched with saturated aqueous NaHCO3
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organics were dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-187bec3cd970485fa881fb8e72392e30
Source dataset
uspto-grants-2015_08
Patent number
US09102643B2

Reaction notes

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