Methyl iodide → HCID 22144888, compound

HRID 1815808Notes

Reaction equation

HRID 1815808 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([Br:12])[C:6]2[O:10][CH:9]=[CH:8][C:7]=2[CH:11]=1.[H-].[Na+].I[CH3:16]>O1CCCC1>[CH3:16][O:1][CH2:2][C:3]1[CH:4]=[C:5]([Br:12])[C:6]2[O:10][CH:9]=[CH:8][C:7]=2[CH:11]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22144918286836-24-6

Product 1

HCID 22144888HCID 22144888, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.372 gm (0.40 mMol) 5-hydroxymethyl-7-bromobenzofuran in tetrahydrofuran was added to a mixture of 1.80 mMol sodium hydride (60% suspension in mineral oil) in 2 mL tetrahydrofuran. After stirring at room temperature for 1 hour, 204 μL iodomethane were added and stirring was continued for 2.5 hours. The reaction mixture was quenched by the addition of water and the resulting mixture was extracted well with ethyl acetate. The organic phase was concentrated under reduced pressure to provide a nearly quantitative yield of the title compound.

Workup

  1. stirringstirring
  2. waitwas continued for 2.5 hours
  3. customThe reaction mixture was quenched by the addition of water
  4. extractionthe resulting mixture was extracted well with ethyl acetate
  5. concentrationThe organic phase was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bcc2b9db773d48909f5eadd245cb6135
Source dataset
uspto-grants-2005_04
Patent number
US06881733B1

Reaction notes

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