Methyl iodide → HCID 69652491, compound

HRID 2215263Notes

Reaction equation

HRID 2215263 reaction equation
[C:1]1([C:7]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[O:8][CH2:9][C@H:10]([OH:21])[CH2:11][S:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH3:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:36]I>O1CCCC1>[C:28]1([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[O:8][CH2:9][C@H:10]([O:21][CH3:36])[CH2:11][S:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH3:20])[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21055313HCID 21055313, compound

Product 1

HCID 69652491HCID 69652491, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

34.8 g (0.076 mol) of 1-(3-triphenylmethyloxy-2-(S)-hydroxypropylthio)-2-methoxybenzene (XII-1), in solution in 50 ml of distilled tetrahydrofuran, are introduced dropwise into a round-bottomed flask, kept under an inert atmosphere, comprising a suspension of 3.5 g of sodium hydride (0.087 mol) in 30 ml of distilled tetrahydrofuran. The mixture is stirred at ambient temperature for 3 hours and then 5.1 ml (0.082 mol) of methyl iodide are added. After stirring at ambient temperature for 2 hours, the mixture is concentrated under reduced pressure and then the residue is taken up in dichloromethane. The solution obtained is cooled and then diluted with ice-cold water. The phases are separated and the aqueous phase is extracted with dichloromethane. The combined organic phases are washed with water and with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue is purified by flash chromatography on silica gel (eluent: dichloromethane/cyclohexane=70:30) to give 35.8 g (0.076 mol) of the title compound (XIII-1) in the form of an oil.

Workup

  1. stirringAfter stirring at ambient temperature for 2 hours
  2. concentrationthe mixture is concentrated under reduced pressure
  3. customThe solution obtained
  4. temperatureis cooled
  5. additiondiluted with ice-cold water
  6. customThe phases are separated
  7. extractionthe aqueous phase is extracted with dichloromethane
  8. washThe combined organic phases are washed with water and with brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe residue is purified by flash chromatography on silica gel (eluent: dichloromethane/cyclohexane=70:30)

Sources & evidence

ORD record
ord-b097051d0c144e3b800e124a8f9703d4
Source dataset
uspto-grants-2006_09
Patent number
US07109234B2

Reaction notes

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