Methanol → HCID 20318254, compound

HRID 866739Notes

Reaction equation

HRID 866739 reaction equation
[OH-:1].[K+].[C:3]([N:7]=[N:8][C:9](Cl)([CH3:19])[CH2:10][CH2:11][C:12]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:13])([CH3:6])([CH3:5])[CH3:4].[CH3:21]O>>[C:3]([N:7]=[N:8][C:9]([O:1][CH3:21])([CH3:19])[CH2:10][CH2:11][C:12]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:13])([CH3:6])([CH3:5])[CH3:4]

Participants

4

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 2031823458496-97-2

Product 1

HCID 20318254HCID 20318254, compoundYield 71%

Procedure

To a stirred solution of 19.7 grams (0.3 moles) of 85% KOH in 150 ml. of methanol cooled in an ice bath was added 80 grams (0.29 moles) of n-butyl 4-t-butylazo-4-chlorovalerate (prepared as in Example XX) dropwise over 1/2 hour. The reaction mixture was stirred an additional 1/2 hour after the addition was complete, poured into 300 ml. of water and extracted with pentane. The pentane solution was washed with water, saturated NaHCO3 solution, water, dried over anhydrous Na2SO4, filtered and the pentane evaporated to leave 55.5 grams (71% yield) of the desired ester.

Workup

  1. additionafter the addition
  2. additionpoured into 300 ml
  3. extractionof water and extracted with pentane
  4. washThe pentane solution was washed with water, saturated NaHCO3 solution, water
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customthe pentane evaporated

Sources & evidence

ORD record
ord-94512afb98884b1db0d6cb081ea647f9
Source dataset
uspto-grants-1978_07
Patent number
US04101522

Reaction notes

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