Methyl iodide → HCID 19426980, compound

HRID 741822Notes

Reaction equation

HRID 741822 reaction equation
[OH:1][C:2]([C:10]1[N:15]=[C:14]([CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH:13]=[CH:12][CH:11]=1)([C:5]1[S:6][CH:7]=[CH:8][N:9]=1)[CH2:3][CH3:4].[CH3:25]I>C1COCC1>[CH3:25][O:1][C:2]([C:10]1[N:15]=[C:14]([CH2:16][O:17][Si:18]([C:21]([CH3:23])([CH3:22])[CH3:24])([CH3:19])[CH3:20])[CH:13]=[CH:12][CH:11]=1)([C:5]1[S:6][CH:7]=[CH:8][N:9]=1)[CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 19427005HCID 19427005, compound

Product 1

HCID 19426980HCID 19426980, compoundYield 156.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of alcohol from Step 1 (740 mg, 2.03 mmol) in 20 mL THF at 0° C. was added KH (466 mg, 4.06 mmol, 35% in oil). After 10 min. MeI (1.44 g, 10.1 mmol) was added dropwise. The solution was stirred for 30 min. at 0° C., then poured into an aqueous saturated NH4C1. The aqueous layer was extracted with EtOAc (3×25 mL) and the combined organic layers were washed with brine and dried over anhydrous MgSO4. Evaporation of the solvent and flash chromatography on silica gel (hexane:EtOAc=9:1) gave the title compound (1.2 g) which was used directly in the next step.

Workup

  1. additionpoured into an aqueous saturated NH4C1
  2. extractionThe aqueous layer was extracted with EtOAc (3×25 mL)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. customEvaporation of the solvent and flash chromatography on silica gel (hexane:EtOAc=9:1)

Sources & evidence

ORD record
ord-3d4c7e56f266450f8e3d999cfd13d47c
Source dataset
uspto-grants-1996_09
Patent number
US05552437

Reaction notes

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