Propargyl alcohol → HCID 22926698, compound

HRID 1985428Notes

Reaction equation

HRID 1985428 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][CH:14]([O:30][CH:31]([CH3:33])[CH3:32])[C:15]([N:17]2[CH:21]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:20][O:19][C:18]2=[O:29])=[O:16])[CH:8]=1)(=O)=O.[CH2:36]([OH:39])[C:37]#[CH:38].C(N(CC)CC)C>CN(C)C=O.[Cu](I)I.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:22]([CH:21]1[CH2:20][O:19][C:18](=[O:29])[N:17]1[C:15](=[O:16])[CH:14]([O:30][CH:31]([CH3:32])[CH3:33])[CH2:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([C:38]#[C:37][CH2:36][OH:39])[CH:8]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 3

HCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 86592577HCID 86592577, compound

Product 1

HCID 22926698HCID 22926698, compoundYield 64.9%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

390 mg of 3-[3-(4-Benzyl-2-(oxo)-oxazolidin-3-yl)-2-isopropoxy-3-oxo-propyl]-phenyl trifluoromethanesulfonate was dissolved in 2 ml of N,N-dimethylformamide, 85 mg of propargyl alcohol, 8 mg of copper iodide, 45 mg of tetrakis (triphenylphosphine) palladium and 0.3 ml of triethylamine were added in succession, and the mixture was stirred overnight at 50° C. under a nitrogen atmosphere. The reaction solution was filtered through silica gel, and the filtrate was dissolved in ethyl acetate, washed with water, 1N hydrochloric acid and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography, to give 207 mg of the title compound as a colorless oil in the 3:2 hexane-ethyl acetate fraction.

Workup

  1. filtrationThe reaction solution was filtered through silica gel
  2. dissolutionthe filtrate was dissolved in ethyl acetate
  3. washwashed with water, 1N hydrochloric acid and saturated brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c4a7017808364ed5b625e2ca0690212a
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

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