Acetic Acid → 2-(4-Methoxybenzyl)thiophene

HRID 1274224Notes

Reaction equation

HRID 1274224 reaction equation
C([Li])CCC.[S:6]1[CH:10]=[CH:9][CH:8]=[CH:7]1.[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Br)=[CH:15][CH:14]=1.C(O)(=O)C>O1CCCC1>[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][C:7]2[S:6][CH:10]=[CH:9][CH:8]=2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8030ThiopheneHCID 1650214-Methoxybenzyl bromideHCID 178418339Butyllithium

Product 1

HCID 110309412-(4-Methoxybenzyl)thiophene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Butyllithium (12.5 ml of 1.6N in hexanes) was added to a stirred solution of thiophene (1.68 g) in dry tetrahydrofuran (80 ml). The mixture was stirred at room temperature for 0.5 h and then a solution of 4-methoxybenzylbromide (2.62 g) in tetrahydrofuran (10 ml) was added dropwise. The mixture was stirred for 1 h and then acetic acid (1.2 ml) was added and the solvent evaporated. The residue was partitioned between ethyl acetate and water, the organic phase was washed with water and brine dried over magnesium sulphate and evaporated. The product was isolated by column chromatography (Kieselgel:hexane). δ(CDCl3) 3.80 (3H, s), 4.10 (2H, s), 6.78-6.94 (4H, m), 7.13-7.20 (3H, m).

Workup

  1. stirringThe mixture was stirred for 1 h
  2. customthe solvent evaporated
  3. customThe residue was partitioned between ethyl acetate and water
  4. washthe organic phase was washed with water and brine
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe product was isolated by column chromatography (Kieselgel:hexane)

Sources & evidence

ORD record
ord-d49cd1b4e3204f63af68cb38b025517f
Source dataset
uspto-grants-2000_12
Patent number
US06156774

Reaction notes

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