Lithium Hydroxide → HCID 178511260, compound

HRID 2402712Notes

Reaction equation

HRID 2402712 reaction equation
[C:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([O:11]C)=[O:10])[CH2:5][CH2:4]1)#[N:2].[OH-].[Li+]>C1COCC1.O>[C:1]([C@H:3]1[CH2:4][CH2:5][C@H:6]([C:9]([OH:11])=[O:10])[CH2:7][CH2:8]1)#[N:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 178501117HCID 178501117, compound

Product 1

HCID 178511260HCID 178511260, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl trans-4-cyanocyclohexanecarboxylate (996 mg, 5.96 mmol) in THF (37 mL) was added a solution of 0.5 M lithium hydroxide in water (20 mL). The mixture was stirred overnight then the THF was removed in vacuo and the residual aqueous solution acidified to pH 4. The resulting mixture was extracted with ether (2×30 mL), EtOAc (2×30 mL) and CHCl3 (2×30 mL) then the combined extracts, dried over anhydrous sodium sulfate and concentrated in vacuo. This material was taken to the next step without any purification. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.43-1.73 (4H, m), 2.05-2.22 (4H, m) and 2.36-2.59 (2H, m).

Workup

  1. customthe THF was removed in vacuo
  2. extractionThe resulting mixture was extracted with ether (2×30 mL), EtOAc (2×30 mL) and CHCl3 (2×30 mL)
  3. dry with materialthe combined extracts, dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThis material was taken to the next step without any purification

Sources & evidence

ORD record
ord-698a5684e9384231875f6871d09a3899
Source dataset
uspto-grants-2014_08
Patent number
US08796455B2

Reaction notes

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