tert-Butanol → HCID 84013601, compound

HRID 1481316Notes

Reaction equation

HRID 1481316 reaction equation
[O:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[O:11])=[CH:2]1.CC([OH:16])(C)C.CC(=CC)C.[O-]Cl=O.[Na+]>O>[O:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]([OH:16])=[O:11])=[CH:2]1

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 105532-Methyl-2-buteneHCID 21794742Furo[2,3-b]pyridine-3-carbaldehydeHCID 23668197Sodium Chlorite

Product 1

HCID 84013601HCID 84013601, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of furo[2,3-b]pyridine-3-carboxaldehyde (67 mmol) [J. Heterocyclic Chem., 23, 1465 (1986)] in 52 mL H2O were added NaH2PO4 (67 mmol), 260 mL t-BuOH, 71 mL 2-methyl-2-butene followed by portionwise addition of NaClO2 (100 mmol) at 0° C. After 15 min, the cooling bath was removed and the reaction was stirred at RT for 24 h. A solution of sat. aq. NaHCO3 was added and the mixture was extracted with EtOAc. The water phase was acidified with 1N HCl solution and it was then extracted 3 times with EtOAc. The combined organic layers were dried over MgSO4 and concentrated in vacuo to obtain the desired compound as beige solid.

Workup

  1. customthe cooling bath was removed
  2. additionA solution of sat. aq. NaHCO3 was added
  3. extractionthe mixture was extracted with EtOAc
  4. extractionwas then extracted 3 times with EtOAc
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-07584ecf2af24ffcb984e42830f28cf5
Source dataset
uspto-grants-2016_08
Patent number
US09409917B2

Reaction notes

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