Pyridine → HCID 14988330, compound

HRID 2291353Notes

Reaction equation

HRID 2291353 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:13]=[CH:12][C:11](I)=[CH:10][CH:9]=1.N1[CH:20]=[CH:19][CH:18]=[CH:17]C=1>C(OCC#[C-])(=O)C.[Cu+].O>[C:2]([O:7][CH2:20][CH2:19][C:18]#[C:17][C:11]1[CH:12]=[CH:13][C:8]([O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)=[CH:9][CH:10]=1)(=[O:1])[CH3:3]

Participants

5

Reactant 2

HCID 1049PyridineHCID 29168032H-Pyran, tetrahydro-2-(4-iodophenoxy)-

Product 1

HCID 14988330HCID 14988330, compound

Reagents, catalysts & solvents 2

HCID 1482747099522-35-7CatalystHCID 962WaterSolvent

Procedure

20 Grams of p-tetrahydropyranyloxyiodobenzene and 70 ml of anhydrous pyridine containing 11.3 g of copper (I) 3-acetyloxy-1-propyn-1-ide were refluxed for 6 hours under an atmosphere of argon gas. After the reaction was completed the reaction mixture was poured into water and the whole mixture was extracted with chloroform. The chloroform layer was washed with water, dried and the solvent was removed by evaporation. The residue thus obtained was purified by means of a silica gel column chromatography (eluent: chlorofrom:n-hexane=1:1) to yield 8 g of 4-[4-(2-tetrahydropyranyloxy)phenyl]-3-butynyl acetate in the form of colorless oily substance.

Workup

  1. extractionthe whole mixture was extracted with chloroform
  2. washThe chloroform layer was washed with water
  3. customdried
  4. customthe solvent was removed by evaporation
  5. customThe residue thus obtained
  6. customwas purified by means of a silica gel column chromatography (eluent: chlorofrom:n-hexane=1:1)

Sources & evidence

ORD record
ord-d5ab9467131b4cc0bce4f5d9379c758a
Source dataset
uspto-grants-1989_01
Patent number
US04795814

Reaction notes

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