Acetone → HCID 14748273, compound

HRID 1165253Notes

Reaction equation

HRID 1165253 reaction equation
O[CH:2]([CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:17][CH:16]=1)[CH2:3][C:4]#[C:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10].CCN(CC)CC.CC(C)=O.[C:37]([OH:40])(=[S:39])[CH3:38]>C1(C)C=CC=CC=1>[C:37]([S:39][CH:2]([CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:17][CH:16]=1)[CH2:3][C:4]#[C:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])(=[O:40])[CH3:38]

Participants

6

Reactant 4

HCID 180AcetoneHCID 8471Triethylamine2×HCID 14748266HCID 14748266, compound2×HCID 178418634HCID 178418634, compound

Product 1

HCID 14748273HCID 14748273, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

In a dry flask equipped with a condenser was placed 4 g of methyl 8-hydroxy-9-(4-pentylphenoxy)-5-nonynoate, the product of Example 8, 1.69 ml of Et3N, 20 ml of toluene and 20 ml of acetone. To the mixture was added 3.43 g of N-methyl-2-fluoropyridimium tosylate stirring at RT for 1 hr. A solution of 0.87 ml of thioacetic acid and 1.69 ml of Et3N in 5 ml of toluene was added. The resulting solution was refluxed for 2 hr. Solvent was removed and the residue was dissolved in Et2O and then was washed with NaHCO3 solution and dried over MgSO4. The crude product, after solvent removal, was purified on a Waters Prep 500 HPLC (EtOAc-hexane 1:16) to obtain the title compound.

Workup

  1. customIn a dry flask equipped with a condenser
  2. temperatureThe resulting solution was refluxed for 2 hr
  3. customSolvent was removed
  4. dissolutionthe residue was dissolved in Et2O
  5. washwas washed with NaHCO3 solution
  6. dry with materialdried over MgSO4
  7. customThe crude product, after solvent removal
  8. customwas purified on a Waters Prep 500 HPLC (EtOAc-hexane 1:16)

Sources & evidence

ORD record
ord-96d704f1325346ad80888def88ecb87c
Source dataset
uspto-grants-1990_03
Patent number
US04908384

Reaction notes

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