Didodecyl 2-(thiophen-3-yl)malonate → Tetradodecyl benzo[1,2-b:4,5-b']dithiophene-4,4,8,8-tetracarboxylate

HRID 335354Notes

Reaction equation

HRID 335354 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]([C:22]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[O:23])[C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:8])=[CH:2]1>CO>[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([C:22]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[O:23])([C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:8])[C:2]3[S:1][CH:5]=[CH:4][C:3]=3[C:6]([C:22]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[O:23])([C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:8])[C:2]1=2

Participants

3

Reactant 1

HCID 70983275Didodecyl 2-(thiophen-3-yl)malonate

Product 1

HCID 86711081Tetradodecyl benzo[1,2-b:4,5-b']dithiophene-4,4,8,8-tetracarboxylateYield 50.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
60 °C

Procedure

In a two-necked flask under argon, a solution of Fe(ClO4)3 in methanol (320 mL) was prepared at 0° C. A dispersion of didodecyl 2-(thiophen-3-yl)malonate in methanol (120 mL) was added to the solution. After the resulting solution was stirred at 60° C. for 4 hours under argon, the solvent was evaporated under vacuum at room temperature. After water (100 mL) was added to the residue, the aqueous layer was extracted with CH2Cl2 (100 mL×2) and the organic layer was dried and concentrated. The crude product was purified by flash chromatography (eluent: CH2Cl2:hexane=3:2) to give tetradodecyl benzo[1,2-b:4,5-b′]dithiophene-4,4,8,8-tetracarboxylate (yield: 9.0 g, 50.2%). 1H NMR (CDCl3); 0.9 (12H, t), 1.3 (72H, m), 1.7 (8H, m), 4.2 (8H, t), 7.3 (2H, d), 7.4 (2H, d).

Workup

  1. customthe solvent was evaporated under vacuum at room temperature
  2. additionAfter water (100 mL) was added to the residue
  3. extractionthe aqueous layer was extracted with CH2Cl2 (100 mL×2)
  4. customthe organic layer was dried
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography (eluent: CH2Cl2:hexane=3:2)

Sources & evidence

ORD record
ord-7d0a6c4e39554c029d5bde7b062ca567
Source dataset
uspto-grants-2014_11
Patent number
US08883954B2

Reaction notes

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