Water → cis-4-Cyanomethyl-5-benzyloxymethylcyclohex-1-ene

HRID 2166423Notes

Reaction equation

HRID 2166423 reaction equation
C1(C)C=CC(S(O[CH2:11][C@H:12]2[C@@H:17]([CH2:18][O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:16][CH:15]=[CH:14][CH2:13]2)(=O)=O)=CC=1.[C-:28]#[N:29].[K+].O>CS(C)=O>[C:28]([CH2:11][C@H:12]1[C@@H:17]([CH2:18][O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:16][CH:15]=[CH:14][CH2:13]1)#[N:29]

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 86740865cis-4-p-Toluene-sulphonyloxymethyl-5-benzyloxymethyl cyclohex-1-ene

Product 1

HCID 67914518cis-4-Cyanomethyl-5-benzyloxymethylcyclohex-1-eneYield 86.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
100 °C

Procedure

The p-toluene sulphonyl ester/benzyl ether (3) (12 g) in dimethylsulphoxide (DMSO) (15 ml) is added with stirring to potassium cyanide (3 g) in DMSO (20 ml). The mixture is heated at 100° C. under nitrogen for 6 hours and is then cooled, poured into water and the product extracted with ether. The solvent is removed and the residue purified on a Florisil column, eluting with petroleum ether-benzene (1:1) to give the title compound as an oil (6.5 g, ca. 80%) νmax (film) 2220 and 1600 cm-1.

Workup

  1. temperatureis then cooled
  2. extractionthe product extracted with ether
  3. customThe solvent is removed
  4. customthe residue purified on a Florisil column
  5. washeluting with petroleum ether-benzene (1:1)

Sources & evidence

ORD record
ord-f921b8ffc25b4c9abb2733e035385e29
Source dataset
uspto-grants-1990_07
Patent number
US04945106

Reaction notes

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