Propargyl alcohol → HCID 69990034, compound

HRID 1250117Notes

Reaction equation

HRID 1250117 reaction equation
[CH2:1]([OH:4])[C:2]#[CH:3].[C:5]([O:9][C:10](=[O:20])[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15](Br)[CH:14]=1)([CH3:8])([CH3:7])[CH3:6].[Cl-].[NH4+]>N1CCCC1.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>[C:5]([O:9][C:10](=[O:20])[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:3]#[C:2][CH2:1][OH:4])[CH:14]=1)([CH3:8])([CH3:7])[CH3:6]

Participants

6

Reactant 3

HCID 7859Propargyl alcoholHCID 25517Ammonium ChlorideHCID 54177962277331-50-7

Product 1

HCID 69990034HCID 69990034, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 31268PyrrolidineSolvent

Conditions

Temperature
77.5 °C

Procedure

Tetrakis(triphenylphosphine)palladium(0) (0.41 g, 0.14 mmol), cuprous iodide (0.5 g, 0.25 mmol), and propargyl alcohol (0.29 mL, 4.91 mmol) were added to a solution of 3-(3-bromophenyl)propionic acid tert-butyl ester (2.13 g, 7.08 mmol) in pyrrolidine (8 mL) under an argon atmosphere at room temperature. The mixture was heated at 75-80° C. for 5 hours. After cooling to room temperature, saturated ammonium chloride was added and the mixture was extracted with diethyl ether. The extract was washed with brine, dried over magnesium sulfate, and concentrated to dryness. Purification by flash chromatography, eluting with hexane/ethyl acetate (85:15), gave 3-[3-(3-hydroxyprop-1-ynyl)phenyl]propionic acid tert-butyl ester as a yellow oil (0.21 g, 33%).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness
  6. customPurification by flash chromatography
  7. washeluting with hexane/ethyl acetate (85:15)

Sources & evidence

ORD record
ord-560699558699436c9a99d163bec44912
Source dataset
uspto-grants-2002_01
Patent number
US06335459B1

Reaction notes

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