HCID 86678076, compound → HCID 86678077, compound

HRID 2369762Notes

Reaction equation

HRID 2369762 reaction equation
[CH2:1]([C:5]1([CH2:36][CH2:37][CH2:38][CH3:39])[C:17]2[CH:16]=[C:15]([C:18]#[C:19][C:20]3[S:24][C:23]([CH:25]=[O:26])=[CH:22][CH:21]=3)[CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][C:8]([C:27]#[C:28][C:29]1[S:33][C:32]([CH:34]=O)=[CH:31][CH:30]=1)=[CH:9][CH:10]=2)[CH2:2][CH2:3][CH3:4].[I-].[CH2:41]([N:47]([CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH3:79])[C:48]1[CH:53]=[CH:52][C:51]([CH2:54][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:50][CH:49]=1)[CH2:42][CH2:43][CH2:44][CH2:45][CH3:46].C(O[K])(C)(C)C>C(Cl)Cl>[CH2:74]([N:47]([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C:48]1[CH:49]=[CH:50][C:51](/[CH:54]=[CH:34]/[C:32]2[S:33][C:29]([C:28]#[C:27][C:8]3[CH:7]=[C:6]4[C:11]([C:12]5[CH:13]=[CH:14][C:15]([C:18]#[C:19][C:20]6[S:24][C:23]([CH:25]=[O:26])=[CH:22][CH:21]=6)=[CH:16][C:17]=5[C:5]4([CH2:36][CH2:37][CH2:38][CH3:39])[CH2:1][CH2:2][CH2:3][CH3:4])=[CH:10][CH:9]=3)=[CH:30][CH:31]=2)=[CH:52][CH:53]=1)[CH2:75][CH2:76][CH2:77][CH2:78][CH3:79]

Participants

5

Reactant 3

HCID 86678076HCID 86678076, compoundHCID 86678078HCID 86678078, compoundHCID 178418922HCID 178418922, compound

Product 1

HCID 86678077HCID 86678077, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 5,5′-(9,9-dibutyl-9H-fluorene-2,7-diyldi-2,1-ethynediyl)bis-2-thiophenecarboxaldehyde (1.14 g, 2.085 mmol) and [[4-(dihexylamino)phenyl]methyl]triphenylphosphonium iodide (1.66 g, 2.501 mmol) in anhydrous CH2Cl2 (40 mL), was added tBuOK (0.352 g, 3.137 mmol). The mixture was stirred at 20° C. for 16 h, then filtered through a short pad of silica gel. The solvent was removed under reduced pressure, and the crude product was purified by column chromatography on silica gel (heptane/CH2Cl2 gradient from 70:30 to 30:70) to yield 701 mg (42%) of 5-[[7-[[5-[(1E)-2-[4-(dihexylamino)phenyl]ethenyl]thien-2-yl]ethynyl]-9,9-dibutyl-9H-fluorene-2-yl]ethynyl]thiophene-2-carboxaldehyde; 1H NMR (300.13 MHz, CDCl3) δ 9.88 (s, 1H), 7.70 (d, J=7.8 Hz, 1H), 7.69 and 7.35 (AX, JAX=3.9 Hz, 2H), 7.68 (d, J=7.8 Hz, 1H), 7.56-7.49 (m, 4H), 7.33 and 6.61 (AA′XX′, JAX=8.9 Hz, 4H), 7.17 and 6.87 (AX, JAX=3.8 Hz, 2H), 6.95 (d, J=16.0 Hz, 1H), 6.86 (d, J=16.0 Hz, 1H), 3.28 (m, 4H), 2.00 (m, 4H), 1.60 (m, 4H), 1.33 (m, 12H), 1.11 (m, 4H), 0.91 (t, J=6.8 Hz, 6H), 0.69 (t, J=7.3 Hz, 6H), 0.59 (m, 4H).

Workup

  1. filtrationfiltered through a short pad of silica gel
  2. customThe solvent was removed under reduced pressure
  3. customthe crude product was purified by column chromatography on silica gel (heptane/CH2Cl2 gradient from 70:30 to 30:70)

Sources & evidence

ORD record
ord-246c2904d9174787be51167078054c0c
Source dataset
uspto-grants-2014_04
Patent number
US08709747B2

Reaction notes

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