Water → HCID 67206584, compound

HRID 1023877Notes

Reaction equation

HRID 1023877 reaction equation
[C:1]([CH:3]1[CH2:8][CH2:7][C:6](=[CH:9][C:10](OCC)=[O:11])[CH2:5][CH2:4]1)#[N:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[OH:11][CH2:10][CH:9]=[C:6]1[CH2:7][CH2:8][CH:3]([C:1]#[N:2])[CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 67205101HCID 67205101, compound

Product 1

HCID 67206584HCID 67206584, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the stirred solution of crude ethyl 2-(4-cyanocyclohexylidene)acetate in THF (12 mL) was added LAH (187 mg, 4.91 mmol) at 10° C. The reaction mixture was allowed to stir at the same temperature for 2 h, water (1.2 mL), aqueous 15% NaOH (1.2 mL), and water (4.0 mL) were each carefully added to the mixture. The resulting slurry was filtered through a pad of Celite and concentrated in vacuo. The crude product was purified by flash column chromatography to afford the desired product as a mixture of isomers. (216 mg, 1.43 mmol, 32%). 1H NMR: 0.94-1.02 (m, 1H), 1.31-1.41 (m, 5H), 1.46-1.61 (m, 9H), 1.73-2.00 (m, 11H), 2.09-2.23 (m, 3H), 2.34-2.48 (m, 3H), 2.78-2.82 (m, 1H), 2.92-2.94 (m, 1H), 3.67-3.72 (m, 3H), 4.15 (d, 2H, J=6.8 Hz), 5.45 (t, 1H, J=6.8 Hz).

Workup

  1. additioneach carefully added to the mixture
  2. filtrationThe resulting slurry was filtered through a pad of Celite
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-37894771799c4b22befbea7d66737636
Source dataset
uspto-grants-2014_05
Patent number
US08722720B2

Reaction notes

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