Water → HCID 23345905, compound

HRID 1856121Notes

Reaction equation

HRID 1856121 reaction equation
[CH2:1]([OH:4])[CH:2]=[CH2:3].N1C=CC=CC=1.[C:11]([N:15]=[N:16][C:17]([C:24]#[N:25])([CH3:23])[CH2:18][CH2:19][C:20](Cl)=[O:21])([CH3:14])([CH3:13])[CH3:12].O>CCOCC>[C:11]([N:15]=[N:16][C:17]([C:24]#[N:25])([CH3:23])[CH2:18][CH2:19][C:20]([O:4][CH2:1][CH:2]=[CH2:3])=[O:21])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7858Allyl AlcoholHCID 152740244-[(E)-tert-Butyldiazenyl]-4-cyanopentanoyl chloride

Product 1

HCID 23345905HCID 23345905, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 2.32 g (0.040 m) of allyl alcohol and 10 ml of pyridine in 50 ml of ether cooled to 10° C. in a 250 ml 4 neck round bottom flask was added a solution of 10 g (0.0435 m) of 4-t-butylazo-4-cyanovaleryl chloride* in 10 ml ether. The acid chloride solution was added dropwise holding the reaction temperature below 20° C. After the addition was complete, the reaction was stirred an additional 2 hours at room temperature and poured into 100 ml water. The ether layer was separated, washed with 20 ml portions of 10% HCl, 10%, NaHCO3 and water. The ether solution was dried over anhydrous sodium sulfate, filtered and the ether evaporated off. The crude produce weighed 8.95 g (89%). The infrared spectra indicated there was a small amount of unreacted acid chloride present in the product. The crude product was purified by column chromatography over alumina using pentane as the eluent. The acid chloride did not come off the column. The pentane was evaporated off to leave the pure product.

Workup

  1. customthe reaction temperature below 20° C
  2. additionAfter the addition
  3. customThe ether layer was separated
  4. washwashed with 20 ml portions of 10% HCl, 10%, NaHCO3 and water
  5. dry with materialThe ether solution was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe ether evaporated off
  8. customThe crude produce
  9. customThe crude product was purified by column chromatography over alumina
  10. customThe pentane was evaporated off
  11. customto leave the pure product

Sources & evidence

ORD record
ord-0354c4a6da2e49f7a94ee6348a733733
Source dataset
uspto-grants-1980_08
Patent number
US04218370

Reaction notes

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