Tetrahydrofuran → HCID 21830688, compound

HRID 1600895Notes

Reaction equation

HRID 1600895 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N:15]12[CH2:22][CH2:21]N([CH2:19][CH2:20]1)CC2.[CH2:23]([Li])CCC.[Cl-].[NH4+].[O:30]1C[CH2:33][CH2:32][CH2:31]1>>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([S:13][CH2:14][CH:31]([OH:30])[CH2:32][CH2:33][C:21]3[CH:22]=[N:15][CH:20]=[CH:19][CH:23]=3)=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 9237DabcoHCID 25517Ammonium ChlorideHCID 21830671HCID 21830671, compoundHCID 178418339Butyllithium

Product 1

HCID 21830688HCID 21830688, compound

Procedure

A stirred solution of 1-cyclohexyl-4-(methylthio)benzene (0.48 g; CA 83:96625v) and 1,4-diazabicyclo[2.2.2]octane (0.267 g) in tetrahydrofuran (40 ml) under nitrogen was cooled to -78° C. under nitrogen. n-Butyllithium (1.6 M in hexanes, 2.1 ml) was added dropwise to this with stirring. After stirring for 1 hour at -10° C. and 1 hour at room temperature the mixture was recooled to -78° C. A solution of 3-(3-pyridyl)-1-propionaldehyde (0.645 g) in tetrahydrofuran (10 ml) was then added. Once addition was complete the reaction was stirred for 15 hours at room temperature before being poured into saturated aqueous ammonium chloride. The mixture was extracted with ether (2×50 ml) and ethyl acetate (1×50 ml), the combined extracts dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with ethyl acetate:dichloromethane (3:1) to give the title compound as a white solid (0.179 g).

Workup

  1. stirringAfter stirring for 1 hour at -10° C. and 1 hour at room temperature the mixture
  2. customwas recooled to -78° C
  3. additionOnce addition
  4. stirringwas stirred for 15 hours at room temperature
  5. extractionThe mixture was extracted with ether (2×50 ml) and ethyl acetate (1×50 ml)
  6. dry with materialthe combined extracts dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography over silica eluting with ethyl acetate:dichloromethane (3:1)

Sources & evidence

ORD record
ord-0540c57da81f44c19601b1d4ae0111e4
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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