Cyclopentanecarbaldehyde → HCID 66661921, compound

HRID 504325Notes

Reaction equation

HRID 504325 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]#[N:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C([Li])CCC.[CH:18]1([CH:23]=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19]1>CCCCCC.C1COCC1>[CH:18]1([CH:23]([OH:24])[C:2]2[CH:7]=[CH:6][C:5]([C:8]3([C:11]#[N:12])[CH2:10][CH2:9]3)=[CH:4][CH:3]=2)[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 3

HCID 70106CyclopentanecarbaldehydeHCID 27952731-(4-Bromophenyl)CyclopropanecarbonitrileHCID 178418339Butyllithium

Product 1

HCID 66661921HCID 66661921, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-30 °C

Procedure

To a solution of 1-(4-bromophenyl)cyclopropanecarbonitrile (2.01 g, 0.00905 mol) in tetrahydrofuran (30 mL, 0.4 mol) was added 2.5 M of n-butyllithium in hexane (4.0 mL) at −78° C. and the mixture was stirred at −30° C. for 30 minutes. A solution of cyclopentanecarbaldehyde (0.972 g, 0.00990 mol) in THF (2 mL) was added to the above mixture and the resulting mixture was stirred at −78° C. for 2 hours. The reaction was then quenched with a small amount of saturated aqueous NH4Cl solution followed by extraction with ethyl acetate, drying with MgSO4, and concentrating under reduced pressure. The crude product was purified by flash chromatography, eluting with 30% AcOEt in hexanes.

Workup

  1. stirringthe resulting mixture was stirred at −78° C. for 2 hours
  2. customThe reaction was then quenched with a small amount of saturated aqueous NH4Cl solution
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialdrying with MgSO4
  5. concentrationconcentrating under reduced pressure
  6. customThe crude product was purified by flash chromatography
  7. washeluting with 30% AcOEt in hexanes

Sources & evidence

ORD record
ord-f99df093ac664092919430cb8592e9e4
Source dataset
uspto-grants-2010_08
Patent number
US07776874B2

Reaction notes

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