Ammonium Chloride → Bis(2-methyl-4-thienyl)methanol

HRID 2216715Notes

Reaction equation

HRID 2216715 reaction equation
[Li]CCCC.[CH3:6][C:7]1[S:8][CH:9]=[C:10](Br)[CH:11]=1.[CH3:13][C:14]1[S:15][CH:16]=[C:17]([CH:19]=[O:20])[CH:18]=1.[NH4+].[Cl-]>CCOCC>[CH3:6][C:7]1[S:8][CH:9]=[C:10]([CH:19]([C:17]2[CH:18]=[C:14]([CH3:13])[S:15][CH:16]=2)[OH:20])[CH:11]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 6385844-Bromo-2-methylthiopheneHCID 65020115-Methylthiophene-3-carbaldehydeHCID 178418339Butyllithium

Product 1

HCID 21943863Bis(2-methyl-4-thienyl)methanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

113 mL of 1.6 M n-BuLi solution (0.18 mol) was added to a solution of 31.3 g of 2-methyl-4-bromo-thiophene (0.177 mol) in 150 mL of ether at −70° C. under stirring. The resulting solution was kept under stirring at −60 to −70° C. for 30 min and then was added of 22.3 g of 2-methyl-4-formyl-thiophene (0.177 mol) in 100 mL of ether. The mixture was allowed to warm to room temperature, then neutralized with 10% aqueous solution of NH4Cl and washed with water. The organic phase was separated and evaporated. The crude bis(2-methyl-4-thienyl)methanol (or 2,2′-dimethyl-4,4′-dithienyl carbinol) was obtained.

Workup

  1. stirringunder stirring at −60 to −70° C. for 30 min
  2. washwashed with water
  3. customThe organic phase was separated
  4. customevaporated

Sources & evidence

ORD record
ord-e22c2322aea04943968a28596d8a5419
Source dataset
uspto-grants-2006_09
Patent number
US07112638B2

Reaction notes

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