Hydrochloric Acid → HCID 14748265, compound

HRID 1165251Notes

Reaction equation

HRID 1165251 reaction equation
[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][CH2:4][C:5]#[CH:6].[Li]CCCC.CCCCCC.[CH2:20]([C:25]1[CH:35]=[CH:34][C:28]([O:29][CH2:30][CH:31]2[CH2:33][O:32]2)=[CH:27][CH:26]=1)[CH2:21][CH2:22][CH2:23][CH3:24].Cl>CN(P(N(C)C)(N(C)C)=O)C>[OH:32][CH:31]([CH2:30][O:29][C:28]1[CH:27]=[CH:26][C:25]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:35][CH:34]=1)[CH2:33][C:6]#[C:5][CH2:4][CH2:3][CH2:2][C:1]([OH:8])=[O:7]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 1430365-Hexynoic acidHCID 14748264HCID 14748264, compoundHCID 178418339Butyllithium

Product 1

HCID 14748265HCID 14748265, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

In a dry flask under N2 was placed 150 ml of HMPA (distilled over NaH) and 15.61 g (0.14 mole) of 5-hexynoic acid, the product of Example 1b, and the mixture cooled in an ice-water bath. A solution of 190 ml of n-BuLi in hexane (0.295 mole) was added dropwise into the flask with stirring. Stirring was continued for an additional 2 hr and 37 g of 2-(4-pentylphenoxymethyl)oxirane, the product of Example 7a, was added. After 2 days stirring, the resulting reaction mixture was poured into an ice water mixture and acidified with 3N HCl. The aqueous solution was extracted with Et2O three times. The organic layers were combined and then washed with aqueous 3N NH4OH. The NH4OH solution was acidified with 3N HCl and was extracted with Et2O. The ether solution was dried over MgSO4 and solvent removed to give an oil. The oil was purified by silical gel column chromatography (CHCl3 -MeOH) and then recrystallized in petroleum ether-EtOAc to give the title compound, mp 54°-57° C.

Workup

  1. customIn a dry flask under N2 was placed
  2. stirringStirring
  3. stirringAfter 2 days stirring
  4. customthe resulting reaction mixture
  5. extractionThe aqueous solution was extracted with Et2O three times
  6. washwashed with aqueous 3N NH4OH
  7. extractionwas extracted with Et2O
  8. dry with materialThe ether solution was dried over MgSO4 and solvent
  9. customremoved
  10. customto give an oil
  11. customThe oil was purified by silical gel column chromatography (CHCl3 -MeOH)
  12. customrecrystallized in petroleum ether-EtOAc

Sources & evidence

ORD record
ord-91ff4c7b94b74a069d09792d6ba213e0
Source dataset
uspto-grants-1990_03
Patent number
US04908384

Reaction notes

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