Methyl iodide → HCID 15182359, compound

HRID 2372462Notes

Reaction equation

HRID 2372462 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:16]2([OH:23])[CH2:21][CH2:20][O:19][CH:18]([CH3:22])[CH2:17]2)[CH:12]=[C:13]([F:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:26]I>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:16]2([O:23][CH3:26])[CH2:21][CH2:20][O:19][CH:18]([CH3:22])[CH2:17]2)[CH:12]=[C:13]([F:15])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 20081943HCID 20081943, compound

Product 1

HCID 15182359HCID 15182359, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (2RS, 4SR)-4-(3-benzyloxy-5-fluorophenyl)-4-hydroxy-2-methyltetrahydropyran (0.45 g) and dimethylformamide (5 ml) cooled in an ice bath, sodium hydride (0.068 g of a 55% w/w dispersion in mineral oil) was added and the mixture was stirred for 45 minutes. Methyl iodide (0.11 ml) was added and the mixture was stirred for 15 minutes. The ice bath was removed and the mixture was stirred at ambient temperature for 30 minutes. The mixture was poured into water (15 ml) and extracted with ethyl acetate (3×15 ml). The combined organic extracts were washed with a saturated aqueous sodium chloride solution, dried (MgSO4) and evaporated. The residue was purified by column chromatography using a 10:1 v/v mixture of toluene and ethyl acetate as eluent. There was thus obtained as an oil, (2RS, 4SR)-4-(3-benzyloxy-5-fluorophenyl)-4-methoxy-2-methyltetrahydropyran (0.33 g, 71%);

Workup

  1. temperaturecooled in an ice bath
  2. stirringthe mixture was stirred for 15 minutes
  3. customThe ice bath was removed
  4. stirringthe mixture was stirred at ambient temperature for 30 minutes
  5. additionThe mixture was poured into water (15 ml)
  6. extractionextracted with ethyl acetate (3×15 ml)
  7. washThe combined organic extracts were washed with a saturated aqueous sodium chloride solution
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customThe residue was purified by column chromatography
  11. additiona 10:1 v/v mixture of toluene and ethyl acetate as eluent

Sources & evidence

ORD record
ord-989fcff442cd48b895b1ef89848ed1c0
Source dataset
uspto-grants-1992_03
Patent number
US05098930

Reaction notes

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