Pyridine → HCID 54329672, compound

HRID 2073705Notes

Reaction equation

HRID 2073705 reaction equation
[CH3:1][C:2]1[O:6][C:5]([CH2:7][CH:8]=[CH:9]Cl)=[CH:4][CH:3]=1.[CH2:11]([OH:14])[C:12]#[CH:13].N1C=CC=CC=1.[O:21]1CCCC1>>[CH3:1][C:2]1[O:6][C:5]([CH:7]=[CH:8][C:9]([O:14][CH2:11][C:12]#[CH:13])=[O:21])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 7859Propargyl alcoholHCID 8028TetrahydrofuranHCID 54470176HCID 54470176, compound

Product 1

HCID 54329672HCID 54329672, compound

Procedure

A solution of 11.5 g of 3-(5-methylfuran-2-yl)-propenyl chloride in 30 ml of absolute tetrahydrofuran was cooled to 0° to 5° C., and 4.2 g of propargyl alcohol and 20 ml of pyridine were added. The mixture was stirred for 12 hours at room temperature, the precipitated hydrochloride was filtered off and concentrated under reduced pressure, and the concentrate taken up in 200 ml of ethyl acetate and 50 ml of water. After washing three times with water, drying over Na2SO4 and removal of the solvent under reduced pressure, the residue was purified chromatographically (toluene/ethyl acetate=1/2). There was obtained 10.9 g of propargyl 3-(5-methylfuran-2-yl)-propenoate; refractive index nD26 =1.578.

Workup

  1. filtrationthe precipitated hydrochloride was filtered off
  2. concentrationconcentrated under reduced pressure
  3. washAfter washing three times with water
  4. dry with materialdrying over Na2SO4 and removal of the solvent under reduced pressure
  5. customthe residue was purified chromatographically (toluene/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-7eb2457c3d0d4832abb64b2eb338d783
Source dataset
uspto-grants-1990_04
Patent number
US04920110

Reaction notes

Loading…