Propargyl alcohol → HCID 11401073, compound

HRID 1061592Notes

Reaction equation

HRID 1061592 reaction equation
[CH2:1]([OH:4])[C:2]#[CH:3].Br[C:6]1[O:7][C:8](Br)=[CH:9][CH:10]=1>C(N)CC.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.[Cu]I>[OH:4][CH2:1][C:2]#[C:3][C:6]1[O:7][C:8]([C:3]#[C:2][CH2:1][OH:4])=[CH:9][CH:10]=1

Participants

6

Reactant 2

HCID 7859Propargyl alcohol2×HCID 108788462,5-dibromofuran

Product 1

HCID 11401073HCID 11401073, compoundYield 95.4%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 7852PropylamineSolvent

Procedure

Pd(Ph3P)4 (580 mg, 3%), CuI (140 mg, 2%) and propargyl alcohol (4.65 ml, 67.7 mmol) are added successively to a solution of 2,5-dibromofuran (5.1 g, 22.6 mmol) in n-propylamine (100 ml), and the mixture is stirred at RT for 1 h and then under reflux for 24 h. More propargyl alcohol (2.0 ml, 33 mmol) is then added and the mixture is stirred under reflux for another 8 h. After cooling, the reaction mixture is filtered off with suction through kieselguhr and washed with ethyl acetate (50 ml). The organic phase is concentrated under reduced pressure. Further purification is carried out by chromatography [Tol/Ac (8:2)] over a silica gel column. This gives the title compound (3.8 g) as a colorless solid. TLC, silica gel (glass plates), [toluene/acetone (8:2)], Rf=0.40.

Workup

  1. temperatureunder reflux for 24 h
  2. stirringthe mixture is stirred
  3. temperatureunder reflux for another 8 h
  4. temperatureAfter cooling
  5. filtrationthe reaction mixture is filtered off with suction through kieselguhr
  6. washwashed with ethyl acetate (50 ml)
  7. concentrationThe organic phase is concentrated under reduced pressure
  8. customFurther purification

Sources & evidence

ORD record
ord-539cd9c952d342438041f66c6603683b
Source dataset
uspto-grants-2005_11
Patent number
US06960588B1

Reaction notes

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