Cyclohexanol → HCID 24698739, compound

HRID 1190969Notes

Reaction equation

HRID 1190969 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH:11]1([OH:17])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.Cl[C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][N:20]=1.C([O-])(O)=O.[Na+]>C1COCC1>[CH:11]1([O:17][C:19]2[N:20]=[CH:21][C:22]([C:23]#[N:24])=[CH:25][CH:26]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 7966CyclohexanolHCID 516892Sodium BicarbonateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 24698739HCID 24698739, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Add sodium bis(trimethylsilyl)amide (3.9 mL, 7.93 mmol, 2M solution in THF) to a solution of cyclohexanol (824 μL, 7.93 mmol) in THF (10 mL). Stir for 30 min at room temperature and then add a solution of 6-chloro-nicotinonitrile (1 g, 7.2 mmol) in anhydrous THF (5 mL). Stir at room temperature overnight and then quench the reaction by addition of saturated aqueous NaHCO3 (100 mL) and extract the aqueous phase with DCM (3×100 mL). Wash the combined organic extracts with brine (100 mL), dry over MgSO4 and concentrate in vacuo to obtain the desired intermediate as a yellow solid (1.04 g, 71%).

Workup

  1. stirringStir at room temperature overnight
  2. customquench
  3. customthe reaction
  4. extractionextract the aqueous phase with DCM (3×100 mL)
  5. washWash the combined organic extracts with brine (100 mL)
  6. dry with materialdry over MgSO4
  7. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-1737371c591e4d83b152affbe583b73f
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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