3-Bromofuran → HCID 19047590, compound

HRID 742489Notes

Reaction equation

HRID 742489 reaction equation
[C:1]([O:4][CH2:5][C:6]#[C:7][C:8]1[CH:12]=[CH:11][O:10][CH:9]=1)(=O)[CH3:2].Br[C:14]1C=CO[CH:15]=1>C1COCC1.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.[Cl-].[Zn+2].[Cl-]>[O:4]1[CH:1]=[CH:2][C:6]([C:7]([C:8]2[CH:12]=[CH:11][O:10][CH:9]=2)=[C:14]=[CH2:15])=[CH:5]1

Participants

6

Reactant 2

HCID 891643-BromofuranHCID 19047585HCID 19047585, compound

Product 1

HCID 19047590HCID 19047590, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-(3-acetyloxy-l-propynyl)furan (1.44 g, 8.7 mmol), 3-bromofuran (2.55 g, 0.017 mol), and Pd(P(C6H5)3)4 (1.0 g, 0.8 mmol) in THF was added added zinc chloride (0.5M in THF, 34 ml, 0.017 mol) and the mixture was stirred at room temperature for 4 hours. The reaction mixture was concentrated in vacuo and the residue was purified by silica column chromatography (methylene chloride/hexane, 2:1) to afford 1.25 g (85%) of [1,1-di(3-furyl)]-1,2-propadiene (Formula III: R3 and R4 together form =CH2 ; R5 =R6 =3-furanyl) as a pale yellow oil.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was purified by silica column chromatography (methylene chloride/hexane, 2:1)

Sources & evidence

ORD record
ord-3340b08ef4ad41a9beaf7005078ff682
Source dataset
uspto-grants-1996_09
Patent number
US05554620

Reaction notes

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