Triethylamine → HCID 178476269, compound

HRID 653355Notes

Reaction equation

HRID 653355 reaction equation
[Cl-].O[NH3+].[C:4]([O:7][CH2:8]/[CH:9]=[CH:10]/[C@H:11]1[CH2:16][CH2:15][C@H:14]([C:17]2[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)(=[O:6])[CH3:5].C([N:27](CC)CC)C.C1(N=C=NC2CCCCC2)CCCCC1>O.N1C=CC=CC=1.C(Cl)Cl.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[C:4]([O:7][CH2:8]/[CH:9]=[CH:10]/[C@H:11]1[CH2:16][CH2:15][C@H:14]([C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:27])=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)(=[O:6])[CH3:5]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 21645Hydroxylamine HClHCID 178476270HCID 178476270, compound

Product 1

HCID 178476269HCID 178476269, compoundYield 114%

Reagents, catalysts & solvents 4

HCID 24463Copper sulfate pentahydrateCatalystHCID 962WaterSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 513 mg of hydroxylammonium chloride in 5 ml of water was placed while gassing with argon in a sulphonation flask provided with a mechanical stirrer and treated at room temperature with a solution of 2.0 g of p-[trans-4-(3-acetoxy-trans-1-propenyl)cyclohexyl]benzaldehyde in 10 ml of pyridine. The mixture was stirred for 1 hour and then treated in sequence with 350 mg of copper sulphate pentahydrate and a solution of 2.1 ml of triethylamine in 10 ml of methylene chloride. After the initially inky blue colour of the copper-pyridine complex had turned olive-green, a solution of 1.74 g of dicyclohexylcarbodiimide in 20 ml of methylene chloride was added. The mixture was subsequently stirred at room temperature for a further 3 hours and then filtered. The filtrate was poured into 100 ml of water and extracted three times with 100 ml of methylene chloride each time. The organic phases were washed twice with 50 ml of water each time, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.5 bar) of the residue (2.75 g) on silica gel with toluene/ethyl acetate (vol. 9:1) gave 2.26 g (114%) of p-[trans-4-(3-acetoxy-trans-1-propenyl)cyclohexyl]benzonitrile as colourless crystals which still contained some dicyclohexylcarbodiimide as the sole impurity. This material was processed without additional purification. Rf-value (toluene/ethyl acetate vol. 9:1) 0.33.

Workup

  1. customwhile gassing with argon in a sulphonation flask
  2. customprovided with a mechanical stirrer
  3. stirringThe mixture was subsequently stirred at room temperature for a further 3 hours
  4. filtrationfiltered
  5. additionThe filtrate was poured into 100 ml of water
  6. extractionextracted three times with 100 ml of methylene chloride each time
  7. washThe organic phases were washed twice with 50 ml of water each time
  8. dry with materialdried over magnesium sulphate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-ea5ae985f12f4c92936e41da159c5698
Source dataset
uspto-grants-1987_06
Patent number
US04676604

Reaction notes

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