Hydrochloric Acid → HCID 18433865, compound

HRID 2187319Notes

Reaction equation

HRID 2187319 reaction equation
[O:1]=[C:2]([CH3:8])[CH2:3][CH2:4][CH2:5][C:6]#[N:7].[Cl-].[Ce+3].[Cl-].[Cl-].[CH:13]1([Mg]Cl)[CH2:17][CH2:16][CH2:15][CH2:14]1.Cl>C1COCC1>[CH:13]1([C:2]([OH:1])([CH3:8])[CH2:3][CH2:4][CH2:5][C:6]#[N:7])[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24636Cerium(III) chlorideHCID 82611Hexanenitrile, 5-oxo-HCID 178478989HCID 178478989, compound

Product 1

HCID 18433865HCID 18433865, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Oxohexanenitrile (11.1 g; 0.10 mmol) was added at 20° C. to a suspension of anhydrous cerium(III) chloride (30 g; 0.12 mol) in THF (250 ml). After 1 hour stirring at room temperature, cyclopentylmagnesium chloride (60 ml of 2.0 M solution in diethyl ether; 0.12 mol) was added dropwise at 5° C. and stirring continued for more 0.5 hour at the same temperature. 2 N HCl (60 ml) was added, and the reaction mixture was extracted with MTBE (2×200 ml). The combined organic phases were washed with 2 N HCl (100 ml), and brine (2×100 ml), dried (MgSO4), and concentrated in vacuo, to give 13 g of crude (83% GC pure; 60% yield) 5-cyclopentyl-5-hydroxyhexanenitrile. The 5-cyclopentyl-5-hydroxyhexanenitrile was used without further purification in the next step.

Workup

  1. stirringstirring
  2. waitcontinued for more 0.5 hour at the same temperature
  3. extractionthe reaction mixture was extracted with MTBE (2×200 ml)
  4. washThe combined organic phases were washed with 2 N HCl (100 ml), and brine (2×100 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eade232202a34e59bca0d10318a728d0
Source dataset
uspto-grants-2002_06
Patent number
US06410000B1

Reaction notes

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