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

HRID 1988403Notes

Reaction equation

HRID 1988403 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-b8e61372ddba4ebe8cacd34b1d40c29d
Source dataset
uspto-grants-2009_06
Patent number
US07553854B2

Reaction notes

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