Iodine → HCID 58526519, Verbindung

HRID 522515

Reaktionsgleichung

Reaktionsgleichung von HRID 522515
[S:1]1[CH:5]=[C:4]([CH:6]=[O:7])[C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][C:2]1=2.[Li+].[Cl-].II.I[C:17]1S[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[C:18]=1C=O.C1(C#C)C=CC=CC=1>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].CCN(CC)CC>[C:19]1([C:18]#[C:17][C:5]2[S:1][C:2]3[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=3[C:4]=2[CH:6]=[O:7])[CH:25]=[CH:24][CH:23]=[CH:22][CH:20]=1

Komponenten

9

Edukt 5

HCID 807IodineHCID 10821PhenylacetyleneHCID 2273281-Benzothiophene-3-carbaldehydeHCID 433294Lithium ChlorideHCID 86659542HCID 86659542, Verbindung

Produkt 1

HCID 58526519HCID 58526519, VerbindungAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel3×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Benzo[b]thiophene-3-carbaldehyde (27) (162 mg, 1.0 mmol) in THF (2 mL) was added to a solution of TMPZnCl.LiCl (2) (1.3 M in THF, 0.85 mL, 1.1 mmol) at 25° C. and the reaction mixture was then stirred at this temperature for 30 min according to TP 2. I2 (381 mg, 1.5 mmol) dissolved in dry THF (2 mL) was then dropwise added and the resulting mixture was stirred for 0.5 h. To the solution of freshly generated in situ 2-iodobenzo[b]thiophene-3-carbaldehyde, NEt3 (7 mL), Cul (8 mg, 4 mol %), Pd(dba)2 (17 mg, 3 mol %) and P(o-furyl)3 (14 mg, 6 mol %) in THF (2 mL) and phenylacetylene (254 mg, 1.5 mol, 1.5 equiv) were successively slowly added. The reaction mixture was stirred at rt for 2 h. The reaction mixture was quenched with a sat. aq. Na2S2O3 solution (10 mL) and with a sat. aq. NH4Cl solution (20 mL), extracted with diethyl ether (3×50 mL) and dried over anhydrous Na2SO4. After filtration, the solvent was evaporated in vacuo. Purification by flash-chromatography (CH2Cl2/n-pentane, 1:2) furnished compound 29c (165 mg, 63%) as a yellowish solid.

Aufarbeitung

  1. additionwas then dropwise added
  2. additionwere successively slowly added
  3. stirringThe reaction mixture was stirred at rt for 2 h
  4. customThe reaction mixture was quenched with a sat. aq. Na2S2O3 solution (10 mL) and with a sat. aq. NH4Cl solution (20 mL)
  5. extractionextracted with diethyl ether (3×50 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationAfter filtration
  8. customthe solvent was evaporated in vacuo
  9. customPurification by flash-chromatography (CH2Cl2/n-pentane, 1:2)

Quellen und Nachweise

ORD-Eintrag
ord-46ec1575041d474d863c095fd3cf2a96
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09334237B2

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