Methyl iodide → HCID 19885891, compound

HRID 654913Notes

Reaction equation

HRID 654913 reaction equation
[H-].[Na+].[OH:3][CH:4]([C:14]1[CH:15]=[C:16]([Si:19]([CH3:22])([CH3:21])[CH3:20])[O:17][CH:18]=1)[CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.I[CH3:24]>O1CCCC1>[CH3:24][O:3][CH:4]([C:14]1[CH:15]=[C:16]([Si:19]([CH3:22])([CH3:21])[CH3:20])[O:17][CH:18]=1)[CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 19885953HCID 19885953, compound

Product 1

HCID 19885891HCID 19885891, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of sodium hydride (0.063 g., 1.05 mmol) in 10 ml tetrahydrofuran at 0° under argon, was added dropwise via syringe 4-(1-hydroxy-4-phenylbutyl)-2-trimethylsilylfuran (0.274 g., 0.951 mmol). This was followed by the addition of iodomethane (0.352 g., 2.48 mmol) and warming of the reaction mixture to room temperature. Several more equivalents of sodium hydride and iodomethane were subsequently added in increments over 2.5 hours until TLC indicated that no starting material remained. The reaction mixture was carefully filtered through celite and partitioned between ethyl ether and 5% hydrochloric acid. The organic portion was washed with 5% sodium bicarbonate, water, saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated to give an oil. Purification by flash chromatography (silica, hexane to 5% ethyl ether/hexane) yielded the desired methyl ether.

Workup

  1. filtrationThe reaction mixture was carefully filtered through celite
  2. custompartitioned between ethyl ether and 5% hydrochloric acid
  3. washThe organic portion was washed with 5% sodium bicarbonate, water, saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an oil
  8. customPurification by flash chromatography (silica, hexane to 5% ethyl ether/hexane)

Sources & evidence

ORD record
ord-7b3878d9d478470c8669f7cc844fda45
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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