Methyl iodide → 5-Methoxymethylbenzo[b]thiophene

HRID 979566Notes

Reaction equation

HRID 979566 reaction equation
[OH-].[K+].[OH:3][CH2:4][C:5]1[CH:13]=[CH:12][C:8]2[S:9][CH:10]=[CH:11][C:7]=2[CH:6]=1.[CH3:14]I>CS(C)=O>[CH3:14][O:3][CH2:4][C:5]1[CH:13]=[CH:12][C:8]2[S:9][CH:10]=[CH:11][C:7]=2[CH:6]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 27954461-Benzothiophen-5-ylmethanol

Product 1

HCID 139229075-Methoxymethylbenzo[b]thiopheneYield 70%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a stirred mixture of powdered KOH (18.9 g, 0.336 mol) in dimethylsulfoxide (100 ml) was added 5-hydroxymethylbenzo[b]thiophene (13.8 g, 0.084 mol) in 25 ml of dimethylsulfoxide. Then methyl iodide (23.9 g, 0.168 mol) was added dropwise at ambient temperature over several minutes. Stirring was continued for 11/2 hours. The mixture was filtered, diluted with water (150 ml) and extracted with methylene chloride (200 ml) in three portions. The combined extracts were washed with water, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. This gave 14.1 g of amber liquid. Distillation gave 10.47 g of colorless liquid, b.p. 2.2 mm Hg 110°-111° C. (Yield 70%).

Workup

  1. custom2 hours
  2. filtrationThe mixture was filtered
  3. additiondiluted with water (150 ml)
  4. extractionextracted with methylene chloride (200 ml) in three portions
  5. washThe combined extracts were washed with water
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. distillationDistillation

Sources & evidence

ORD record
ord-2667776d311648c490241a339c91f0da
Source dataset
uspto-grants-1987_05
Patent number
US04668697

Reaction notes

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