1,5-Dibromopentane → Ethyl 1-cyanocyclohexane-1-carboxylate

HRID 2370493Notes

Reaction equation

HRID 2370493 reaction equation
[C:1]([CH2:3][C:4]([O-:6])=[O:5])#[N:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]Br.[C:20](OCC)(=O)[CH3:21]>CN(C=O)C>[CH2:20]([O:5][C:4]([C:3]1([C:1]#[N:2])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:6])[CH3:21]

Participants

6

Reactant 4

HCID 81001,5-DibromopentaneHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 1551036Cyanoacetate

Product 1

HCID 10997650Ethyl 1-cyanocyclohexane-1-carboxylateYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of cyanoacetate (1 eq) in DMF at 0° C. was slowly added cesium carbonate (2.5 eq), followed by the slow addition of 1,5-dibromopentane. This mixture was allowed to stir for 30 minutes at 0° C. and at room temperature for two hours. The crude reaction mixture was diluted with ethyl acetate and washed three times with water, dried with anhydrous sodium sulfate, filtered, and concentrated. The compound was clean enough to continue without purification. 57% yield. 1H NMR (300 MHz, CDCl3) δ 4.25 (q, 2H), 2.12-1.68 (m, 10H), 1.31 (t, 3H).

Workup

  1. customat 0° C.
  2. customThe crude reaction mixture
  3. washwashed three times with water
  4. dry with materialdried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto continue without purification

Sources & evidence

ORD record
ord-ef71bd26a36446e39e320f0c876b8149
Source dataset
uspto-grants-2014_04
Patent number
US08710048B2

Reaction notes

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