Potassium Hydroxide → HCID 46175564, compound

HRID 455977Notes

Reaction equation

HRID 455977 reaction equation
C(OC(=O)[NH:5][C:6]1[C:11]([F:12])=[CH:10][CH:9]=[C:8]([O:13][C:14]([F:17])([F:16])[F:15])[C:7]=1[C:18]#[C:19][Si](C)(C)C)C.[OH-].[K+]>CC(O)(C)C>[F:12][C:11]1[CH:10]=[CH:9][C:8]([O:13][C:14]([F:15])([F:16])[F:17])=[C:7]2[C:6]=1[NH:5][CH:19]=[CH:18]2

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 46175563HCID 46175563, compound

Product 1

HCID 46175564HCID 46175564, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4 (28.9 g, 79.6 mmol) and KOH (35.7 g, 636.7 mmol) in degassed t-BuOH (300 mL) is heated at 70° C. overnight. LC/MS indicates the reaction is completed. The mixture is cooled to rt, and then partitioned between H2O and Et2O. The two layers are separated, and the aqueous layer was extracted with Et2O (2×). The combined organic layers are washed with H2O and brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude material is purified on silica gel with heptane/EtOAc (100/0 to 60/40) as eluant to give 16 g (91%) of 5 as a yellow liquid. 1H NMR (CDCl3) δ 8.47 (br s, 1H), 7.35-7.20 (m, 1H), 6.95-6.80 (m, 2H), 6.68 (d, J=2.5 Hz, 1H); 19F NMR (CDCl3) δ −57.63 (s, 3F), −136.10 (d, J=8.5 Hz, 1F); MS 220 (M+1, 100%), 200.

Workup

  1. temperatureThe mixture is cooled to rt
  2. custompartitioned between H2O and Et2O
  3. customThe two layers are separated
  4. extractionthe aqueous layer was extracted with Et2O (2×)
  5. washThe combined organic layers are washed with H2O and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude material is purified on silica gel with heptane/EtOAc (100/0 to 60/40) as eluant

Sources & evidence

ORD record
ord-d8279f7518f74254ab257a8dd223c69d
Source dataset
uspto-grants-2013_07
Patent number
US08497379B2

Reaction notes

Loading…