Hexane → HCID 67342290, compound

HRID 451566Notes

Reaction equation

HRID 451566 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10].CCCCCC.[F:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=1.[Cl-].[NH4+]>O1CCCC1>[F:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]([OH:26])[C:3]2[C:2]([NH:7][C:8](=[O:13])[C:9]([CH3:10])([CH3:12])[CH3:11])=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 25517Ammonium ChlorideHCID 680234-FluorobenzaldehydeHCID 10515192-(Pivaloylamino)pyridine

Product 1

HCID 67342290HCID 67342290, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of N-(pyridin-2-yl)pivalamide (1.84 g, 10 mmol) in tetrahydrofurane (100 mL) was added at −78° C. under an atmosphere of nitrogen 1.6 M butyl lithium in hexane (13.1 mL, 21 mmol). The reaction is slighly exothermic and a yellow color appears. The reaction is warmed to 0° C. within 15 minutes and stirred at 0° C. for 2 hours. A white suspension is formed. The reaction is cooled to −78° C. and 4-fluorobenzaldehyde (1.52 g, 1.29 mL, 12.0 mmol) was added in tetrahydrofurane (6.55 mL). The reaction was warmed to room temperature over night to yield an orange suspension. Saturated aqueous ammonium chloride solution was added and the reaction was extracted twice with ethyl acetate and once with methylene chloride. The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure. The title compound was obtained as a yellow viscous oil (1.058 g, 35%) after purification by column chromatography on silica gel using a gradient from CH2Cl2 to CH2Cl2/MeOH 19:1 (v/v) as eluent. MS ISP (m/e): 303.1 (100) [(M+H)+].

Workup

  1. customA white suspension is formed
  2. temperatureThe reaction is cooled to −78° C.
  3. temperatureThe reaction was warmed to room temperature over night
  4. customto yield an orange suspension
  5. extractionthe reaction was extracted twice with ethyl acetate and once with methylene chloride
  6. washThe combined organic layers were washed with saturated aqueous sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b2db706dff7a49ef9a4a7d5fe0175013
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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