Aluminum(III) Chloride → 3-[(3,6-dihydro-4-phenyl-1(2H)-pyridinyl)methyl]cyclohexanone

HRID 1034196Notes

Reaction equation

HRID 1034196 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].O1[C:15]2([CH2:20][CH2:19][CH2:18][CH:17]([C:21]([N:23]3[CH2:28][CH:27]=[C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH2:25][CH2:24]3)=O)[CH2:16]2)[O:14]CC1>C(OCC)C.O1CCCC1>[C:29]1([C:26]2[CH2:27][CH2:28][N:23]([CH2:21][CH:17]3[CH2:18][CH2:19][CH2:20][C:15](=[O:14])[CH2:16]3)[CH2:24][CH:25]=2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 103590941-(1,4-Dioxaspiro[4.5]dec-7-yl carbonyl)-1,2,3,6-tetrahydro-4-phenylpyridineHCID 21226445Aluminium lithium hydride

Product 1

HCID 117778783-[(3,6-dihydro-4-phenyl-1(2H)-pyridinyl)methyl]cyclohexanone

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of aluminum chloride (14.54 g) in 500 mL of anhydrous diethyl ether is added dropwise to a suspension of lithium aluminum hydride (12.4 g) in 500 mL of tetrahydrofuran. The mixture is stirred at room temperature for 30 minutes. A solution of 1-(1,4-dioxaspiro[4.5]dec-7-yl carbonyl)-1,2,3,6-tetrahydro-4-phenylpyridine (Step B) in 500 mL of tetrahydrofuran is added dropwise. The mixture is stirred at room temperature overnight, and it is quenched by careful addition of 13 mL of water, followed by 59 mL of 25% aqueous sodium hydroxide solution. The resulting mixture is stirred at room temperature for 2 hours, filtered through celite, and concentrated in vacuo. The title compound is obtained (90.40 g) as a light yellow oil (silica; Rf =0.2; 1% methanol, 99% chloroform).

Workup

  1. stirringThe mixture is stirred at room temperature overnight
  2. customit is quenched by careful addition of 13 mL of water
  3. stirringThe resulting mixture is stirred at room temperature for 2 hours
  4. filtrationfiltered through celite
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-52a5c3097d2847768560ec5d1fa38d23
Source dataset
uspto-grants-1994_05
Patent number
US05314896

Reaction notes

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