Water → HCID 67268225, compound

HRID 252453Notes

Reaction equation

HRID 252453 reaction equation
[CH:1]1([C@H:7]([CH2:20][CH:21]=[CH2:22])[CH2:8]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C-:23]#[N:24].[Na+].O>CS(C)=O>[CH:1]1([C@H:7]([CH2:20][CH:21]=[CH2:22])[CH2:8][C:23]#[N:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 87332210HCID 87332210, compound

Product 1

HCID 67268225HCID 67268225, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

To the crude product, (S)-toluene-4-sulfonic acid 2-cyclohexyl-pent-4-enyl ester, in DMSO (40 mL) was added NaCN, and the resulting mixture was heated at 90° C. for 1.5 h. The reaction mixture was cooled to room temperature and treated with H2O (20 mL). The reaction mixture was then extracted with diethylether (3×25 mL), dried (MgSO4) and concentrated in vacuo to yield a residue which was purified by Kugelrohr distillation (0.19 mm Hg, 80-90° C.) to yield (R)-3-cyclohexyl-hex-5-enenitrile.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe reaction mixture was then extracted with diethylether (3×25 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto yield a residue which
  6. distillationwas purified by Kugelrohr distillation (0.19 mm Hg, 80-90° C.)

Sources & evidence

ORD record
ord-93080c8f1d5a4e80a30959e829576f96
Source dataset
uspto-grants-2011_01
Patent number
US07868022B2

Reaction notes

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