Methanesulfonic Acid → Tetradecylthiophene-3-carboxylate

HRID 523438

Reaction equation

HRID 523438 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]([O:8][CH3:9])=[O:7])=[CH:2]1.[CH2:10](O)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]C.CS(O)(=O)=O>C1(C)C=CC=CC=1>[CH2:9]([O:8][C:6]([C:3]1[CH:4]=[CH:5][S:1][CH:2]=1)=[O:7])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH3:10]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 82091-TetradecanolHCID 574151Methyl 3-thiophenecarboxylate

Product 1

HCID 86717683Tetradecylthiophene-3-carboxylateYield 92.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a 200 mL round bottom flask were added 10 g (70 mmol) of methyl 3-thiophenecarboxylate, 17 g (79 mmol) of 1-tetradecanol, 1 mL methanesulfonic acid, and 50 mL of toluene. This mixture was heated to reflux for 17 hours. After the solvent was removed, the remaining methyl 3-thiophenecarboxylate was removed by kugelrohr distillation. The remaining residue was filtered through a silica gel pad with 10% ethyl acetate in hexane. The solvents were removed from the filtrate to provide 21 g of the desired compound. The NMR data were obtained and were consistent with those of the desired compound.

Workup

  1. temperatureThis mixture was heated
  2. temperatureto reflux for 17 hours
  3. customAfter the solvent was removed
  4. customthe remaining methyl 3-thiophenecarboxylate was removed by kugelrohr distillation
  5. filtrationThe remaining residue was filtered through a silica gel pad with 10% ethyl acetate in hexane
  6. customThe solvents were removed from the filtrate

Sources & evidence

ORD record
ord-5c036f0e1c7740fa8b0fc7e2cf1fadfa
Source dataset
uspto-grants-2016_05
Patent number
US09337358B2

Linked notes

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