Triethylsilane → HCID 178502736, compound

HRID 1485103Notes

Reaction equation

HRID 1485103 reaction equation
[Si]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]([N:17]([O:19][CH3:20])[CH3:18])=[O:16])[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.C([SiH](CC)CC)C.[Bi](Br)(Br)Br.[F:32][C:33]1[CH:40]=[CH:39][C:36]([CH:37]=O)=[CH:35][CH:34]=1.C(=O)([O-])O.[Na+]>C(#N)C.C(OCC)(=O)C>[F:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37][O:8][C@H:9]2[CH2:10][CH2:11][C@H:12]([C:15]([N:17]([O:19][CH3:20])[CH3:18])=[O:16])[CH2:13][CH2:14]2)=[CH:35][CH:34]=1

Participants

8

Reactant 5

HCID 12052TriethylsilaneHCID 680234-FluorobenzaldehydeHCID 82232bismuth(III) bromideHCID 516892Sodium BicarbonateHCID 178502738HCID 178502738, compound

Product 1

HCID 178502736HCID 178502736, compoundYield 62.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution in acetonitrile (11 mL) of the compound (1.00 g) obtained in step (2) above, triethylsilane (579 mg) was added. Bismuth tribromide (104 mg) and 4-fluorobenzaldehyde (617 mg) were added under cooling with ice and the mixture was stirred at room temperature for two hours. To the reaction mixture, a saturated aqueous solution of sodium hydrogencarbonate and ethyl acetate were added and the insoluble matter was removed by filtration through Celite (registered trademark). The organic layer in the filtrate was separated and washed with saturated brine. The washed organic layer was dried over anhydrous magnesium sulfate and after removing the desiccant by filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=100:0-50:50) to give the titled compound as a colorless oil (0.61 g).

Workup

  1. temperatureunder cooling with ice
  2. customthe insoluble matter was removed by filtration through Celite (registered trademark)
  3. customThe organic layer in the filtrate was separated
  4. washwashed with saturated brine
  5. dry with materialThe washed organic layer was dried over anhydrous magnesium sulfate
  6. customafter removing the
  7. filtrationdesiccant by filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=100:0-50:50)

Sources & evidence

ORD record
ord-54906bf9c1934e50b9a2d1814099c01c
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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