Propargyl alcohol → HCID 19967144, compound

HRID 976345Notes

Reaction equation

HRID 976345 reaction equation
Br[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH2:13]([OH:16])[C:14]#[CH:15].C(NCC)C>C1C=CC=CC=1.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:16][CH2:13][C:14]#[C:15][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7859Propargyl alcoholHCID 8021DiethylamineHCID 22043Ethyl 4-bromobenzoate

Product 1

HCID 19967144HCID 19967144, compoundYield 34.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 241BenzeneSolvent

Procedure

2.5 g of tetrakis(triphenylphosphine)palladium (0) was added to 50 ml of a solution of 10 g of ethyl p-bromobenzoate in benzene at room temperture. The obtained mixture was stirred at that temperature for one hour, followed by the addition thereto of 2.5 g of propargyl alcohol, 0.84 g of cuprous iodide and 19 g of diethylamine. The obtained mixture was stirred at room temperature for 26 hours and filtered through Celite. Water (50 ml) was added to the filtrate and the obtained mixture was extracted with ethyl acetate. The organic phase was washed with a 10% aqueous solution of hydrochloric acid and a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate and distilled to remove the solvent. The residue was purified by silica gel chromatography (developer: 20% ethyl acetate/n-hexane) to give 3.1 g of the title compound as a pale-yellow solid.

Workup

  1. additionfollowed by the addition
  2. stirringThe obtained mixture was stirred at room temperature for 26 hours
  3. filtrationfiltered through Celite
  4. additionWater (50 ml) was added to the filtrate
  5. extractionthe obtained mixture was extracted with ethyl acetate
  6. washThe organic phase was washed with a 10% aqueous solution of hydrochloric acid
  7. dry with materiala saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate
  8. distillationdistilled
  9. customto remove the solvent
  10. customThe residue was purified by silica gel chromatography (developer: 20% ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-aadb42f60448428cbc1d257af9ada3b2
Source dataset
uspto-grants-1997_03
Patent number
US05612356

Reaction notes

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