Pyridine → HCID 53986375, compound

HRID 918301Notes

Reaction equation

HRID 918301 reaction equation
[CH2:1]([OH:5])[CH2:2][C:3]#[CH:4].N1C=CC=CC=1.[CH2:12]([C:15]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([O:19][CH3:20])[C:16](Cl)=[O:17])[CH:13]=[CH2:14]>C1C=CC=CC=1>[CH2:12]([C:15]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([O:19][CH3:20])[C:16]([O:5][CH2:1][CH2:2][C:3]#[CH:4])=[O:17])[CH:13]=[CH2:14]

Participants

5

Reactant 3

HCID 1049PyridineHCID 135663-Butyn-1-OLHCID 53863032HCID 53863032, compound

Product 1

HCID 53986375HCID 53986375, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Into a solution of 1.4 g of 3-butyn-1-ol and 20 g of pyridine in 20 cc of benzene, was added a solution of 4.5 g of α-allyl-α-methoxyphenyl acetic chloride in 10 cc of benzene while being cooled with ice, whereby white precipitates were deposited immediately. The reaction mixture was washed with a diluted hydrochloric acid, 5% aqueous solution of sodium carbonate and an aqueous solution saturated with sodium chloride, and dried over anhydrous sodium sulfate. Evaporation of benzene gave 4.6 g of oily 3-butynyl α-allyl-α -methoxyphenylacetate, nD25 1.5137.

Workup

  1. temperaturewhile being cooled with ice, whereby
  2. customwhite precipitates
  3. washThe reaction mixture was washed with a diluted hydrochloric acid, 5% aqueous solution of sodium carbonate
  4. dry with materialan aqueous solution saturated with sodium chloride, and dried over anhydrous sodium sulfate
  5. customEvaporation of benzene

Sources & evidence

ORD record
ord-0ee4844a165045fb944ccafb500e56ed
Source dataset
uspto-grants-1976_07
Patent number
US03970703

Reaction notes

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