Toluene → HCID 13671387, compound

HRID 1380906Notes

Reaction equation

HRID 1380906 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:8]([C:15]1[N:20]=[C:19]([CH:21]=[O:22])[CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C1(C)C([S:29](Cl)(=[O:31])=[O:30])=CC=CC=1.[C-:34]#[N:35].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[S:29]([C:4]1[CH:5]=[CH:6][C:1]([CH3:7])=[CH:2][CH:3]=1)([O:22][CH:21]([C:34]#[N:35])[C:19]1[CH:18]=[CH:17][CH:16]=[C:15]([O:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:20]=1)(=[O:31])=[O:30]

Participants

7

Reactant 4

HCID 1140TolueneHCID 8623o-Toluenesulfonyl chlorideHCID 8929Sodium Cyanide2×HCID 129410066-Phenoxypyridine-2-carbaldehyde

Product 1

HCID 13671387HCID 13671387, compound

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A 25 ml roundbottom flask equipped with a dropping funnel, thermometer and stirring bar was charged with 6 ml of toluene, 5 g of 6-phenoxy-2-pyridinecarboxaldehyde and 4.41 g of toluenesulfonyl chloride. The dropping funnel was charged with 10 ml of water, 1.2 g of sodium cyanide and 50 mg of tetrabutylammonium chloride. The solution was cooled to 0° C. and the sodium cyanide solution was added dropwise over 25 minutes. The temperature was controlled to about 4° C. as the solution turned pink and exothermic. The solution was allowed to stand at 4° C. for 1/2 hour. The reaction mixture was poured into 150 ml of water and extracted with four 75 ml portions of diethyl ether. The combined extract was washed with two 150 ml portions of water, dried (MgSO4) and stripped to give a crude amber oil. The crude oil product was chromatographed using 1:1 methylene chloride/hexane as eluent to yield 4.2 g of the desired product as an amber oil.

Workup

  1. customA 25 ml roundbottom flask equipped with a dropping funnel
  2. customwas controlled to about 4° C. as the solution
  3. extractionextracted with four 75 ml portions of diethyl ether
  4. extractionThe combined extract
  5. washwas washed with two 150 ml portions of water
  6. dry with materialdried (MgSO4)
  7. customto give a crude amber oil
  8. customThe crude oil product was chromatographed

Sources & evidence

ORD record
ord-737725d070244fef87bf014fbc34220d
Source dataset
uspto-grants-1986_04
Patent number
US04584304

Reaction notes

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