Propargyl alcohol → HCID 15789203, compound

HRID 1721900Notes

Reaction equation

HRID 1721900 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][CH:3]=1.[CH2:9]([OH:12])[C:10]#[CH:11]>C(NCC)C.[Cu]I>[I:8][C:5]1[CH:6]=[CH:7][C:2]([C:11]#[C:10][CH2:9][OH:12])=[CH:3][CH:4]=1

Participants

5

Reactant 2

HCID 7859Propargyl alcoholHCID 12208p-Diiodobenzene

Product 1

HCID 15789203HCID 15789203, compoundYield 63.4%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8021DiethylamineSolvent

Procedure

A mixture of 1,4-diiodobenzene (24.7 g), propargyl alcohol (1.68 g), BTPC (0.21 g) and CuI (28 mg) in diethylamine (180 ml) was stirred at room temperature under nitrogen for 18 h. The solvent was evaporated in vacuo at 35°, the residual solid taken up in MC (200 ml) and the solution washed with 2N hydrochloric acid (150 ml). The aqueous phase was extracted with further MC (75 ml), the organic layers combined, dried and purified by FCC eluting with EA-CX (1:6) and then EA-CX (1:3) to yield the title compound as fawn crystalline solid (4.9 g) m.p. 101°-102°.

Workup

  1. customThe solvent was evaporated in vacuo at 35°
  2. washthe solution washed with 2N hydrochloric acid (150 ml)
  3. extractionThe aqueous phase was extracted with further MC (75 ml)
  4. customdried
  5. custompurified by FCC
  6. washeluting with EA-CX (1:6)

Sources & evidence

ORD record
ord-a16292567b1e43d68fd44d9146f394fa
Source dataset
uspto-grants-1989_08
Patent number
US04853382

Reaction notes

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