Hydrofluoric Acid → HCID 86714670, compound

HRID 1409460Notes

Reaction equation

HRID 1409460 reaction equation
[Si]([O:18][CH:19]([C:21]1[N:25]=[C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[O:23][N:22]=1)[CH3:20])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.F.C([O-])(O)=O.[Na+]>C1COCC1.N1C=CC=CC=1>[OH:18][CH:19]([C:21]1[N:25]=[C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[O:23][N:22]=1)[CH3:20]

Participants

6

Reactant 3

HCID 14917Hydrofluoric AcidHCID 516892Sodium BicarbonateHCID 70981482HCID 70981482, compound

Product 1

HCID 86714670HCID 86714670, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 3-(1-((tert-butyldiphenylsilyl)oxy)ethyl)-1,2,4-oxadiazole-5-carboxylate (5.90 mmol, 2.5 g) was dissolved in THF and cooled to 0° C. with an ice bath. 70% Hydrogen fluoride in pyridine (1.5 ml) was added slowly. After addition, the reaction mixture was stirred at ambient temperature for overnight. The reaction mixture was basified by aqueous NaHCO3 solution and extracted with DCM. The organic layers were washed with water, dried, filtered and evaporated. The product was purified by flash-chromatography. Yield 897 mg. 1H-NMR (400 MHz; CDCl3): δ 1.46 (t, 3H), 1.66 (d, 3H), 4.53 (q, 2H), 5.11 (q, 1H).

Workup

  1. additionAfter addition
  2. extractionextracted with DCM
  3. washThe organic layers were washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe product was purified by flash-chromatography

Sources & evidence

ORD record
ord-fc6f0bb745c4447ea61c349828ae88ac
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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