Propiolic Acid → HCID 18981479, compound

HRID 1441154Notes

Reaction equation

HRID 1441154 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]1([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:29](O)(=[O:32])[C:30]#[CH:31]>CN(C)C1C=CN=CC=1.CCOCC>[C:29]([O:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:32])[C:30]#[CH:31]

Participants

6

Reactant 3

HCID 10110Propiolic AcidHCID 10868DicyclohexylcarbodiimideHCID 5201106-Phenyl-1-hexanol

Product 1

HCID 18981479HCID 18981479, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

Under a nitrogen atmosphere at -20° C., a mixture of 1.3 g of dicyclohexylcarbodiimide, 0.051 g of 4-dimethylaminopyridine in 15 ml of dried ether is added dropwise, with stirring, to a mixture of 1 g of 6-phenylhexanol and 0.43 g of propiolic acid in 15 ml of dried ether. After the addition was over, the reaction solution was warmed to the room temperature and stirred at the room temperature for ten hours. After the reaction was completed, the reaction solution was filtered. The filtrate was washed twice with cold 1N hydrochloric acid and twice with a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. After removal of the solvent under reduced pressure, the obtained residue was subjected to silicagel column chromatography to yield 0.788 g of 6-phenylhexyl propiolate (compound 2).

Workup

  1. additionis added dropwise
  2. additionAfter the addition
  3. filtrationthe reaction solution was filtered
  4. washThe filtrate was washed twice with cold 1N hydrochloric acid and twice with a saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-ce534b85d4744c229e357f74b663e6f9
Source dataset
uspto-grants-1996_03
Patent number
US05502242

Reaction notes

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