Methyl iodide → HCID 69416149, compound

HRID 1351248Notes

Reaction equation

HRID 1351248 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH2:14][CH2:13][CH2:12][C:11](=[O:15])[C:8]=2[S:9][CH:10]=1)=[O:5])[CH3:2].[CH3:16][Si](C)(C)[N-][Si](C)(C)C.[Li+].O1CCCC1.CI.[Cl-].[NH4+]>O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH2:14][CH2:13][CH:12]([CH3:16])[C:11](=[O:15])[C:8]=2[S:9][CH:10]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 13356239HCID 13356239, compoundHCID 23714775LiHMDS tetrahydrofuran

Product 1

HCID 69416149HCID 69416149, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

To a solution of 7-oxo-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester (the compound of Preparation Example 3) (1.0 g) in tetrahydrofuran (9 mL) was added dropwise 1.0M lithium hexamethyldisilazide-tetrahydrofuran solution (4.9 mL). After stirring at −70° C. for 15 minutes, methyl iodide (0.34 mL) was added and the solution was warmed to room temperature and was stirred for 30 minutes. After an aqueous solution of saturated ammonium chloride was added and a further dilution with water, extraction was carried out with ethyl acetate. After the organic layer was washed with saturated sodium chloride water and dried with anhydrous sodium sulfate, the residue that was obtained upon removing the solvent by evaporation was purified by silica gel column chromatography (hexane/ethyl acetate), and the title compound (426 mg) was obtained as a colorless solid.

Workup

  1. temperaturethe solution was warmed to room temperature
  2. stirringwas stirred for 30 minutes
  3. extractiona further dilution with water, extraction
  4. washAfter the organic layer was washed with saturated sodium chloride water
  5. dry with materialdried with anhydrous sodium sulfate
  6. customthe residue that was obtained
  7. customupon removing the solvent
  8. customby evaporation
  9. customwas purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-fbf60a571675486e84d83fe72ac14764
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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