Water → HCID 20144490, compound

HRID 649019Notes

Reaction equation

HRID 649019 reaction equation
[OH:1][CH2:2][C:3]1[C:4]2[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:5]=2[S:6][CH:7]=1.[H-].[Na+].[CH3:15]I.O>O1CCCC1>[CH3:15][O:1][CH2:2][C:3]1[C:4]2[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:5]=2[S:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 601251HCID 601251, compound

Product 1

HCID 20144490HCID 20144490, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

400 mg of 3-hydroxymethyl-7-methyl-benzo[b]thiophene are dissolved in tetrahydrofuran, mixed with 82 mg of NaH (80%) and after addition of 48 mg of methyl iodide heated for half an hour at 50° C. The reaction mixture is mixed with water, repeatedly extracted and the organic phase washed, dried and concentrated on a rotary evaporator. The residue is chromatographed over silica-gel (eluant: toluene/glacial acetic acid=95:5) to yield the title compound as an oil.

Workup

  1. extractionrepeatedly extracted
  2. washthe organic phase washed
  3. customdried
  4. concentrationconcentrated on a rotary evaporator
  5. customThe residue is chromatographed over silica-gel (eluant: toluene/glacial acetic acid=95:5)

Sources & evidence

ORD record
ord-758441cac6344ee9bd39678053277b5d
Source dataset
uspto-grants-1988_04
Patent number
US04737516

Reaction notes

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