Stannane, [2,2'-bithiophen]-5-yltributyl- → 4-Formyl-5-hydroxymethyl-2,2':5', 2"-terthiophene

HRID 1599512Notes

Reaction equation

HRID 1599512 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[S:10][C:9]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)=[CH:8][CH:7]=1)CCC.[CH:24]([C:26]1[CH:30]=[C:29](I)[S:28][C:27]=1[CH2:32][OH:33])=[O:25]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.O1CCCC1>[CH:24]([C:26]1[CH:30]=[C:29]([C:6]2[S:10][C:9]([C:11]3[S:12][CH:13]=[CH:14][CH:15]=3)=[CH:8][CH:7]=2)[S:28][C:27]=1[CH2:32][OH:33])=[O:25]

Participants

5

Reactant 2

HCID 11201877Stannane, [2,2'-bithiophen]-5-yltributyl-HCID 189288892-(Hydroxymethyl)-5-iodothiophene-3-carbaldehyde

Product 1

HCID 573213644-Formyl-5-hydroxymethyl-2,2':5', 2"-terthiopheneYield 38%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a two-necked round bottomed flask was added 5-tributylstannyl-2,2'-bithiophene (2.04 g), bis(triphenylphosphine)palladium (II) chloride (0.19 g), 3-formyl-2-hydroxymethyl-5-iodo-thiophene (1.0 g) and tetrahydrofuran (20 ml). The reaction mixture was refluxed for 16 hours. Extracted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was separated by silica gel chromatography, eluted with n-hexane/ethyl acetate (9:1→1:1 gradient) to give brownish solid product (0.43 g, 38%), melting point 108°-110° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 16 hours
  2. extractionExtracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was separated by silica gel chromatography
  7. washeluted with n-hexane/ethyl acetate (9:1→1:1 gradient)

Sources & evidence

ORD record
ord-39c20772fcec42f3b22ab542dcb257ec
Source dataset
uspto-grants-1998_04
Patent number
US05741811

Reaction notes

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