Pentane → HCID 20318253, compound

HRID 866738Notes

Reaction equation

HRID 866738 reaction equation
[C:1]([N:5]=[N:6][C:7](Cl)([CH3:17])[CH2:8][CH2:9][C:10]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:11])([CH3:4])([CH3:3])[CH3:2].CCCCC.[C:24]1([Mg]Br)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CCOCC>[C:1]([N:5]=[N:6][C:7]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([CH3:17])[CH2:8][CH2:9][C:10]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:11])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8003PentaneHCID 2031823458496-97-2HCID 178418255HCID 178418255, compound2×

Product 1

HCID 20318253HCID 20318253, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a clean, dry, 500 ml, 4-neck round bottom flask equipped with a mechanical stirrer, thermometer, condenser with drying tube and under a nitrogen atmosphere was added a solution of 70 grams (0.253 moles) of n-butyl 4-t-butylazo-4-chlorovalerate (prepared as in Example XX) in 200 ml. of pentane and the solution cooled to 5° C. With rapid stirring 86.6 ml. (0.26 moles) of a 3 molar solution of phenylmagnesium bromide in ether was added from a dropping funnel over 1/2 hour holding the reaction temperature at 10°-15° C with an ice bath. After the addition was complete, the reaction was stirred for an additional 45 minutes at 15° C. Ice chips were then added to the stirred reaction until the excess phenylmagnesium bromide was destroyed. The reaction mixture was then stirred into 200 ml. of 5% HCl until the magnesium salts dissolved. The pentane layer was separated, washed with 5% HCl, water, dried over anhydrous sodium sulfate, filtered and the pentane evaporated to leave 53 grams (66% yield) of product.

Workup

  1. customTo a clean, dry
  2. custom500 ml, 4-neck round bottom flask equipped with a mechanical stirrer
  3. customthermometer, condenser with drying tube
  4. customat 10°-15° C
  5. additionAfter the addition
  6. stirringthe reaction was stirred for an additional 45 minutes at 15° C
  7. customwas destroyed
  8. stirringThe reaction mixture was then stirred into 200 ml
  9. dissolutionof 5% HCl until the magnesium salts dissolved
  10. customThe pentane layer was separated
  11. washwashed with 5% HCl, water
  12. dry with materialdried over anhydrous sodium sulfate
  13. filtrationfiltered
  14. customthe pentane evaporated

Sources & evidence

ORD record
ord-068d4d31d5984e319388a2702315ef29
Source dataset
uspto-grants-1978_07
Patent number
US04101522

Reaction notes

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