Tetrahydrofuran → HCID 136337803, compound

HRID 876436Notes

Reaction equation

HRID 876436 reaction equation
[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([O:21][Si](C(C)(C)C)(C)C)[C:14]([Br:20])=[CH:15][CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.C1COCC1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>CCOC(C)=O>[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([OH:21])[C:14]([Br:20])=[CH:15][CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 67234839HCID 67234839, compound

Product 1

HCID 136337803HCID 136337803, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To the product from Step E (2.8 g, 6.15 mmol) was added THF (60 mL). The solution was cooled to 0° C. then TBAF.3H2O (2.33 g, 7.38 mmol) was added and the mixture was stirred for 1 hour. The mixture was then diluted with EtOAc (100 mL) and then washed with saturated aqueous NaHCO3 (75 mL). The layers were separated and the aqueous phase washed with EtOAc (100 mL). The combined organic phases were washed with brine and dried over Na2SO4, filtered and concentrated. The crude mixture was triturated with MeOH and filtered. The solid was washed with Et2O to provide 0.730 g (35%) of product.

Workup

  1. addition3H2O (2.33 g, 7.38 mmol) was added
  2. washwashed with saturated aqueous NaHCO3 (75 mL)
  3. customThe layers were separated
  4. washthe aqueous phase washed with EtOAc (100 mL)
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude mixture was triturated with MeOH
  10. filtrationfiltered
  11. washThe solid was washed with Et2O

Sources & evidence

ORD record
ord-5a691deca499423482ba541dec5f89ca
Source dataset
uspto-grants-2015_03
Patent number
US08987251B2

Reaction notes

Loading…