Propargyl alcohol → HCID 19261287, compound

HRID 549872Notes

Reaction equation

HRID 549872 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.N12CCCN=C1CCCCC2.[CH2:22]([OH:25])[C:23]#[CH:24]>O1CCCC1.CCOCC.[Cu]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>[CH:8]1([C:5]2[CH:6]=[CH:7][C:2]([C:24]#[C:23][CH2:22][OH:25])=[CH:3][CH:4]=2)[CH2:10][CH2:9]1

Participants

8

Reactant 3

HCID 7859Propargyl alcoholHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 122213551-Bromo-4-cyclopropylbenzene

Product 1

HCID 19261287HCID 19261287, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To a degassed solution of 1-bromo-4-cyclopropylbenzene (4.4 g, 22.3 mmol; prepared according to J. Org. Chem. 1976, 41, 2262) in anhydrous tetrahydrofuran (22 mL), copper(I) iodide (134 mg, 0.70 mol) and tetrakis(triphenylphosphine)palladium (773 mg, 0.67 mmol) were added and the mixture was cooled down with ice bath. 1,8-Diazabicyclo[5.4.0]-undec-7-ene (4 mL, 26.8 mmol) was added and the reaction mixture was degassed again. A degassed solution of prop-2-yn-1-ol (1.56 mL, 26.8 mmol) in anhydrous tetrahydrofuran (3 mL) was added dropwise afterwards and the reaction mixture was stirred at 50° C. over night under nitrogen. After cooling, the mixture was diluted with ether (100 mL) and washed with water (40 mL) and 15% hydrochloric acid (2×40 mL). The aqueous layer was extracted with ether (5×40 mL). Combined organic extracts were finally washed with 10% aqueous solution of sodium hydrogen carbonate (40 mL) and brine (2×40 mL) and dried with anhydrous magnesium sulfate. The crude product was purified by column chromatography (silica gel Fluka 60, hexanes/ethyl acetate 10:1-8:1) yielding 3-(4-cyclopropylphenyl)prop-2-yn-1-ol as yellow oil, which solidified in refrigerator.

Workup

  1. temperaturethe mixture was cooled down with ice bath
  2. customthe reaction mixture was degassed again
  3. temperatureAfter cooling
  4. washwashed with water (40 mL) and 15% hydrochloric acid (2×40 mL)
  5. extractionThe aqueous layer was extracted with ether (5×40 mL)
  6. washCombined organic extracts were finally washed with 10% aqueous solution of sodium hydrogen carbonate (40 mL) and brine (2×40 mL)
  7. dry with materialdried with anhydrous magnesium sulfate
  8. customThe crude product was purified by column chromatography (silica gel Fluka 60, hexanes/ethyl acetate 10:1-8:1)

Sources & evidence

ORD record
ord-32a3460bf2eb49bcb4694c9adf43b621
Source dataset
uspto-grants-2011_05
Patent number
US07943613B2

Reaction notes

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