Potassium Cyanide → HCID 54380125, compound

HRID 1580273Notes

Reaction equation

HRID 1580273 reaction equation
CS(O)(=O)=O.[CH2:6]1[O:24][C:9]2([CH2:14][CH2:13][C:12]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)([CH2:15]O)[CH2:11][CH2:10]2)[O:8][CH2:7]1.[C-]#[N:26].[K+]>CN(C)P(N(C)C)(N(C)C)=O>[CH2:6]1[O:24][C:9]2([CH2:14][CH2:13][C:12]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)([C:15]#[N:26])[CH2:11][CH2:10]2)[O:8][CH2:7]1

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 86732935HCID 86732935, compound

Product 1

HCID 54380125HCID 54380125, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A mixture of 18.6 g. (0.055 M) of 4-benzyl-4-hydroxymethylcyclohexan-1-one ethylene ketal methanesulfonate (2) (prepared as in Example 2C) and 18 g. of potassium cyanide in 180 ml. of hexamethylphosphoramide is heated for about 17 hours in an oil bath at about 145° C. The resulting gel is allowed to cool, diluted to 800 ml. with water and extracted with benzene. The organic layer is washed with water and brine and evaporated to dryness. The residue is chromatographed on 1 l. of silica gel and eluted with 25% ethyl acetate in Skellysolve B and the fractions found similar to TLC pooled to give 4-benzyl-4-cyanocyclohexan-1-one ethylene ketal (3).

Workup

  1. additionA mixture of 18.6 g
  2. temperatureto cool
  3. additiondiluted to 800 ml
  4. extractionwith water and extracted with benzene
  5. washThe organic layer is washed with water and brine
  6. customevaporated to dryness
  7. customThe residue is chromatographed on 1 l
  8. washof silica gel and eluted with 25% ethyl acetate in Skellysolve B

Sources & evidence

ORD record
ord-23ad8edd6cce437091c876b6304d8b90
Source dataset
uspto-grants-1976_01
Patent number
US03932425

Reaction notes

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