Propargyl alcohol → HCID 22926886, compound

HRID 1985289Notes

Reaction equation

HRID 1985289 reaction equation
[CH:1]([O:4][CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14](OS(C(F)(F)F)(=O)=O)[CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])([CH3:3])[CH3:2].[CH2:26]([OH:29])[C:27]#[CH:28].C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C.[Cu](I)I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:29][CH2:26][C:27]#[C:28][C:14]1[CH:13]=[C:12]([CH2:11][CH:5]([O:4][CH:1]([CH3:3])[CH3:2])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 3

HCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 57719687HCID 57719687, compound

Product 1

HCID 22926886HCID 22926886, compoundYield 44.3%

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

550 mg of Ethyl 2-isopropoxy-3-(3-[(trifluoromethyl)sulfonyl]oxyphenyl)propanoate was dissolved in 5 ml of N,N-dimethylformamide, and 160 mg of propargyl alcohol, 13 mg of copper iodide, 83 mg of tetrakis(triphenylphosphine)palladium and 1 ml of triethylamine were added. After stirring was continued at 50° C. for 4 hours under nitrogen atmosphere, the reaction mixture was diluted with ethyl acetate and washed with water and 1N hydrochloric acid. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off. Then, the residue was purified by silica gel column chromatography, to give 184 mg of the title compound in the 4:1→2:1 hexane-ethyl acetate fraction.

Workup

  1. washwashed with water and 1N hydrochloric acid
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. distillationthe solvent was distilled off
  5. customThen, the residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d4c9b138bdd844eaa35e3feca357b29c
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

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