Ethyl propiolate → HCID 22609540, compound

HRID 2306791Notes

Reaction equation

HRID 2306791 reaction equation
FC(F)(F)S(O[C:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][C:11]([O:19][CH3:20])=[C:12]([O:17][CH3:18])[CH:13]=2)[CH:8]=1)(=O)=O.[C:23]([O:27][CH2:28][CH3:29])(=[O:26])[C:24]#[CH:25].C([O-])(=O)C.[Na+]>CN(C)C=O.CC([O-])=O.CC([O-])=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd+2]>[CH3:18][O:17][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][C:11]=1[O:19][CH3:20])[CH:8]=[C:7]([C:25]#[C:24][C:23]([O:27][CH2:28][CH3:29])=[O:26])[CH2:16][CH2:15]2

Participants

6

Reactant 3

HCID 12182Ethyl propiolateHCID 517045Sodium AcetateHCID 22609583HCID 22609583, compound

Product 1

HCID 22609540HCID 22609540, compound

Reagents, catalysts & solvents 2

HCID 84538Palladium(2+) acetate--triphenylphosphane (1/2/2)CatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 178 mg (0.53 mmol) of (3,4-dihydro-6,7-dimethoxy-2-naphthyl) trifluoromethane-sulfonate in dimethylformamide (2 ml) were added 0.39 ml (3.9 mmol) of ethyl 2-propynoate, 84.8 mg (1.0 mmol) of sodium acetate and 14.8 mg (0.020 mmol) of bis(triphenylphosphine)-palladium (II) acetate with stirring under nitrogen, and the mixture was stirred for 1 hour and 30 minutes at 60° C. A saturated saline solution was added to the reaction mixture to conduct extraction with benzene-hexane (1:2). An organic layer was washed with a saturated saline solution, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resultant crude oil was purified by column chromatography on silica gel to obtain 76.5 mg (yield: 51%) of crude crystals of the title compound. The crude crystals were recrystallized from diethyl ether-hexane, thereby obtaining a pale yellow crystalline powder.

Workup

  1. stirringthe mixture was stirred for 1 hour and 30 minutes at 60° C
  2. additionA saturated saline solution was added to the reaction mixture
  3. extractionextraction with benzene-hexane (1:2)
  4. washAn organic layer was washed with a saturated saline solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resultant crude oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c23127acffa447cfbb4e01a8ba8491b5
Source dataset
uspto-grants-2004_12
Patent number
US06828316B2

Reaction notes

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