Triethylamine → 2-Dec-1-ynyl-3-decanyldithieno[2,3-d:2',3'-d']thieno [3,2-b:4,5-b']dithiophene

HRID 1367447

Reaktionsgleichung

Reaktionsgleichung von HRID 1367447
BrC1[S:18][C:5]2[C:6]3[S:14][C:13]4[C:12]5[S:15][CH:16]=[CH:17][C:11]=5[S:10][C:9]=4[C:7]=3[S:8][C:4]=2[C:3]=1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].[CH:29]#[C:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38].[CH2:39](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>[C:30]([C:29]1[S:18][C:5]2[C:6]3[S:14][C:13]4[C:12]5[S:15][CH:16]=[CH:17][C:11]=5[S:10][C:9]=4[C:7]=3[S:8][C:4]=2[C:3]=1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])#[C:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 129971-DecyneHCID 669248622-Bromo-3-decanyldithieno[2,3-d:2',3'-d']thieno[3,2-b:4,5-b']dithiophene

Produkt 1

HCID 669248432-Dec-1-ynyl-3-decanyldithieno[2,3-d:2',3'-d']thieno [3,2-b:4,5-b']dithiopheneAusbeute 90,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

2-Bromo-3-decanyldithieno[2,3-d:2′,3′-d′]thieno[3,2-b:4,5-b′]dithiophene (2.16 g, 4.6 mmol) (106) was mixed with 1-decyne (1.27 g, 9.2 mmolmol), tetrakis(triphenylphosphine)palladium (0.27 g, 0.23 mmol) and copper(I) iodide (0.087 g, 0.46 mmol) in triethylamine (50 mL). This mixture was bubbled with nitrogen for 5 minutes and then heated up to 130° C. under argon for 16 hours. The 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 eluted with hexane to produce the target compound (2.3 g, 90.2%). 1HNMR: Solvent CD2Cl2. δ 7.41 (d, 1H), 7.33 (d, 1H), 2.84 (t, 2H), 2.23 (t, 2H), 1.73-1.27 (m, 28H), 0.89 (m, 6H).

Aufarbeitung

  1. customThis mixture was bubbled with nitrogen for 5 minutes
  2. customThe triethylamine 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 materialdried over MgSO4
  8. customThe solvent was removed in vacuo
  9. customthe residue was purified by chromatography on silica gel
  10. washeluted with hexane

Quellen und Nachweise

ORD-Eintrag
ord-a265aed53b1c4fe3a58e0958294b9f59
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893191B2

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