Water → HCID 67514860, compound

HRID 2176066Notes

Reaction equation

HRID 2176066 reaction equation
[H-].[Na+].[S:3]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[C:10]3[S:16][CH:15]=[C:14]([CH2:17][C:18]4[CH:22]=[CH:21][S:20][CH:19]=4)[C:11]=3[S:12][CH:13]=2)=[CH:4]1.[CH2:23](Br)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].O>C1COCC1>[S:20]1[CH:21]=[CH:22][C:18]([C:17]([C:14]2[C:11]3[S:12][CH:13]=[C:9]([C:8]([C:5]4[CH:6]=[CH:7][S:3][CH:4]=4)([CH2:7][CH2:6][CH2:5][CH2:8][CH2:9][CH2:10][CH2:11][CH3:14])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:10]=3[S:16][CH:15]=2)([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:19]1

Participants

6

Reactant 4

HCID 962WaterHCID 81401-BromooctaneHCID 24758Sodium hydrideHCID 67515331HCID 67515331, compound

Product 1

HCID 67514860HCID 67514860, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium hydride in THF is added a THF solution of 3,6-bis(thiophen-3-ylmethyl)thieno[3,2-b]thiophene. Octyl bromide is then added and the mixture is refluxed until reaction completion, as determined by TLC. The reaction is then poured into cold water, extracted with MTBE and combined organic phases are washed with water. After drying the organic phase with magnesium sulfate and filtering through Buchner the solvent is evaporated. The resulting product can be purified by column chromatography.

Workup

  1. temperaturethe mixture is refluxed until reaction completion
  2. extractionextracted with MTBE
  3. washare washed with water
  4. dry with materialAfter drying the organic phase with magnesium sulfate
  5. filtrationfiltering through Buchner the solvent
  6. customis evaporated
  7. customThe resulting product can be purified by column chromatography

Sources & evidence

ORD record
ord-aa0209553c8a41ce9d83369446179d80
Source dataset
uspto-grants-2015_06
Patent number
US09062152B2

Reaction notes

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