Allyltributylstannane → HCID 70062133, compound

HRID 1417244Notes

Reaction equation

HRID 1417244 reaction equation
Br[C:2]1[CH:10]=[C:9]([O:11][CH3:12])[C:5]2[O:6][CH:7]=[CH:8][C:4]=2[CH:3]=1.[CH2:13]([Sn](CCCC)(CCCC)CCCC)[CH:14]=[CH2:15]>CN(C)C=O.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>[CH2:15]([C:2]1[CH:10]=[C:9]([O:11][CH3:12])[C:5]2[O:6][CH:7]=[CH:8][C:4]=2[CH:3]=1)[CH:14]=[CH2:13]

Participants

5

Reactant 2

HCID 90628AllyltributylstannaneHCID 11009684HCID 11009684, compound

Product 1

HCID 70062133HCID 70062133, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 10 g (0.044 mol) of 5-bromo-7-methoxybenzo[b]furan, 17.5 g (0.053 mol) of allyltributyltin and 1.02 g (0.00088 mol) of tetrakis(triphenylphosphine)palladium(0) in 80 ml of dimethylformamide is heated at 90° C. for 15 hours under an inert atmosphere. After returning to room temperature, the dimethylformamide is evaporated off in vacuo. The reaction mass is taken up in 200 ml of diethyl ether and washed in succession with 100 ml of water and 100 ml of a saturated sodium chloride solution. Customary treatment of the organic phase yields an oil, which is purified by chromatography on a silica column using a dichloromethane/heptane (6/4) mixture as eluant.

Workup

  1. customAfter returning to room temperature
  2. customthe dimethylformamide is evaporated off in vacuo
  3. washwashed in succession with 100 ml of water and 100 ml of a saturated sodium chloride solution
  4. customCustomary treatment of the organic phase yields an oil, which
  5. customis purified by chromatography on a silica column

Sources & evidence

ORD record
ord-eb4b6859f26a4ed4af880bc2ef6a1e88
Source dataset
uspto-grants-1999_03
Patent number
US05877190

Reaction notes

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