Methyl iodide → 4-Methoxy-4-[3-(tetrahydropyran-2-yloxy)prop-1-ynyl]tetrahydropyran

HRID 21899Notes

Reaction equation

HRID 21899 reaction equation
[H-].[Na+].[OH:3][C:4]1([C:10]#[C:11][CH2:12][O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.[H][H].[CH3:22]I>C1COCC1>[CH3:22][O:3][C:4]1([C:10]#[C:11][CH2:12][O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[CH2:5][CH2:6][O:7][CH2:8][CH2:9]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 193880334-Hydroxy-4-[3-(tetrahydropyran-2-yloxy)prop-1-ynyl]tetrahydropyranHCID 178418361HCID 178418361, compound

Product 1

HCID 199309164-Methoxy-4-[3-(tetrahydropyran-2-yloxy)prop-1-ynyl]tetrahydropyranYield 96.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (1.2 g of an 80% oil dispersion, 50 mmol) in dry THF (45 mL) was added a solution of 4-hydroxy-4-[3-(tetrahydropyran-2-yloxy)-prop-1-ynyl]tetrahydropyran(3.71 g, 15.3 mmol), prepared as in step 1. After hydrogen evolution ceased, methyl iodide (3.0 mL, 48.2 mmol) was added neat and the resulting solution was stirred overnight at ambient temperature. The reaction was quenched by addition of crushed ice and saturated aqueous NH4Cl. The resulting two-phase mixture was extracted with ether (3×100 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. Purification by chromatography on silica gel (100 g, 10% ethyl acetate: hexanes) provided 4-methoxy-4-[3-(tetrahydropyran-2-yloxy)prop-1-ynyl]tetrahydropyran (3.74 g, 95 %) as a colorless oil.

Workup

  1. additionwas added
  2. customThe reaction was quenched by addition of crushed ice and saturated aqueous NH4Cl
  3. extractionThe resulting two-phase mixture was extracted with ether (3×100 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by chromatography on silica gel (100 g, 10% ethyl acetate: hexanes)

Sources & evidence

ORD record
ord-8d87aed1f81544aabf499a42c61158c1
Source dataset
uspto-grants-1995_06
Patent number
US05426111

Reaction notes

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