Tetrahydrofuran → HCID 22610116, compound

HRID 432862Notes

Reaction equation

HRID 432862 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1C(C1CCCCC1)C.[Li+].[CH3:16][CH2:17][CH2:18][CH2-:19].[CH2:20]([O:22][CH:23]([O:26][CH2:27][CH3:28])[CH2:24]Br)[CH3:21].[CH2:29]1[CH2:33]O[CH2:31][CH2:30]1>>[CH2:20]([O:22][CH:23]([O:26][CH2:27][CH3:28])[CH:24]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[CH:17]([CH:18]1[CH2:31][CH2:30][CH2:29][CH2:33][CH2:19]1)[CH3:16])[CH3:21]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 61028n-Butyl lithiumHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 22610115HCID 22610115, compound

Product 1

HCID 22610116HCID 22610116, compoundYield 46%

Conditions

Temperature
-78 °C

Procedure

2-Pyridyl-1-cyclohexylethane (2 g, 10.6 mmol, prepared above) was dissolved in THF (20 mL) and cooled to −78° C. N-Butyllithium (13 mL of a 1.6 M solution in THF, 21.2 mmol) was added to the cooled solution. After stirring for 10 minutes, the cooling bath was removed and after 10 minutes, when the reaction had reached room temperature, it was re-cooled to −78° C. Bromoacetaldehyde diethyl acetal (2.1 g, 10.6 mmol) was then added and after one hour the cooling bath was removed. After 1.5 hours, n-Bu4NBr was added and the reaction was then stirred overnight. Water was then added and the quenched reaction was extracted with ethyl acetate (3 times). The organic extracts were combined, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by flash chromatography to provide 2-pyridyl-3-cyclohexyl-butyraldehyde diethyl acetal (1.5 g, 46%).

Workup

  1. customthe cooling bath was removed and after 10 minutes
  2. customhad reached room temperature
  3. temperatureit was re-cooled to −78° C
  4. customwas removed
  5. waitAfter 1.5 hours
  6. additionn-Bu4NBr was added
  7. stirringthe reaction was then stirred overnight
  8. additionWater was then added
  9. customthe quenched reaction
  10. extractionwas extracted with ethyl acetate (3 times)
  11. dry with materialdried over anhydrous sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated under vacuum
  14. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-9d65882f2a1d45a4b79345af138b28a1
Source dataset
uspto-grants-2003_12
Patent number
US06664274B1

Reaction notes

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