Ethyl propiolate → HCID 22609540, compound

HRID 1250965Notes

Reaction equation

HRID 1250965 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.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[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 178419050HCID 178419050, compoundCatalystHCID 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-8e2282ca49544acfa04a6a64e9608663
Source dataset
uspto-grants-2002_01
Patent number
US06340682B1

Reaction notes

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