Methyl iodide → HCID 59774928, compound

HRID 2422490Notes

Reaction equation

HRID 2422490 reaction equation
[CH3:1][Si:2]([C:5]#[C:6][C:7]1([OH:13])[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1)([CH3:4])[CH3:3].[H-].[Na+].I[CH3:17]>C1COCC1.CN(C=O)C>[CH3:17][O:13][C:7]1([C:6]#[C:5][Si:2]([CH3:3])([CH3:4])[CH3:1])[CH2:8][CH2:9][O:10][CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 597748681044277-44-2

Product 1

HCID 59774928HCID 59774928, compound

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

To a cooled solution (0° C.) of 4-{(trimethylsilyl)ethynyl}tetrahydropyran-4-ol prepared as described in the above example (2.5 g, 12.6 mmol) in a THF-DMF mixture (55 mL, 10:1), sodium hydride (60% suspension in oil, 0.504 g, 12.6 mmol) was added portionwise. After addition, the mixture was stirred 15 minutes before iodomethane (0.788 mL, 12.6 mmol) was added. The temperature was slowly raised to room temperature and the reaction was stirred for another 2 hours. The reaction mixture was then quenched with water and the product was extracted with ethyl acetate (2×). The combined organic layers were diluted with hexanes and washed with water and brine, dried over MgSO4, filtered and concentrated. The crude residue obtained was purified by column chromatography (acetone/dichloromethane, 2:98) to afford the title compound. 1H NMR (400 MHz, acetone-d6): 3.82-3.74 (m, 2H), 3.61-3.54 (m, 2H), 3.34 (s, 3H), 1.90-1.82 (m, 2H), 1.71-1.63 (m, 2H), 0.21 (s, 9H).

Workup

  1. additionwas added portionwise
  2. additionAfter addition
  3. additionwas added
  4. customThe reaction mixture was then quenched with water
  5. extractionthe product was extracted with ethyl acetate (2×)
  6. additionThe combined organic layers were diluted with hexanes
  7. washwashed with water and brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude residue obtained
  12. customwas purified by column chromatography (acetone/dichloromethane, 2:98)

Sources & evidence

ORD record
ord-11a7fcd3a91b49c2a3a05e7d2a1e60ea
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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