1-Decyne → 3-Decanyl-6-dec-1-ynyldithieno[3,2-b:2',3'-d]thiophene

HRID 1175101

Reaktionsgleichung

Reaktionsgleichung von HRID 1175101
Br[C:2]1[S:12][C:5]2[C:6]3[S:11][CH:10]=[CH:9][C:7]=3[S:8][C:4]=2[C:3]=1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[CH:23]#[C:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>C(N(CC)CC)C.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.[Cu]I>[CH2:13]([C:3]1[C:4]2[S:8][C:7]3[CH:9]=[C:10]([C:23]#[C:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[S:11][C:6]=3[C:5]=2[S:12][CH:2]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Komponenten

6

Edukt 2

HCID 129971-DecyneHCID 161034752-Bromo-3-decanyldithieno[3,2-b:2',3'-d]thiophene

Produkt 1

HCID 669250153-Decanyl-6-dec-1-ynyldithieno[3,2-b:2',3'-d]thiopheneAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

2-bromo-3-decanyldithieno[3,2-b:2′,3′-d]thiophene (92)(4.16 g, 0.01 mol) was mixed with 1-decyne (3.6 g, 0.026 mol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol) and copper(I) iodide (0.19 g, 1.0 mmol) in triethylamine (80 mL). This mixture was bubbled with nitrogen for 5 minutes and then heated up to 130° C. under argon for 16 hours. Triethylamine was evaporated and hexane (150 mL) was added. This mixture was filtered to remove solid salts. The organic layer was washed with 1 M hydrochloric acid (50 mL) and brine (50 mL) then dried over MgSO4. The solvent was removed in vacuo, and the residue was purified by chromatography on silica gel eluting with hexane to yield the target compound (3.87 g, 93.0%). 1H NMR, solvent CD2Cl2. δ 7.36 (d, 1H), 7.30 (d, 1H), 2.82 (t, 2H), 2.49 (t, 2H), 1.63-1.27 (m, 28H), 0.88 (m, 6H).

Aufarbeitung

  1. customThis mixture was bubbled with nitrogen for 5 minutes
  2. customTriethylamine was evaporated
  3. additionhexane (150 mL) was added
  4. filtrationThis mixture was filtered
  5. customto remove solid salts
  6. washThe organic layer was washed with 1 M hydrochloric acid (50 mL) and brine (50 mL)
  7. dry with materialthen dried over MgSO4
  8. customThe solvent was removed in vacuo
  9. customthe residue was purified by chromatography on silica gel eluting with hexane

Quellen und Nachweise

ORD-Eintrag
ord-19d7fa4606f246688414790cf03f8782
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07838623B2

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