Iodoethane → 3-Ethoxy-4,4-dimethoxytetrahydro-2H-pyran

HRID 1044556Notes

Reaction equation

HRID 1044556 reaction equation
[CH3:1][O:2][C:3]1([O:10][CH3:11])[CH2:8][CH2:7][O:6][CH2:5][CH:4]1[OH:9].[H-].[Na+].I[CH2:15][CH3:16]>C1COCC1>[CH2:15]([O:9][CH:4]1[C:3]([O:10][CH3:11])([O:2][CH3:1])[CH2:8][CH2:7][O:6][CH2:5]1)[CH3:16]

Participants

5

Reactant 3

HCID 6340Iodoethane2×HCID 24758Sodium hydride2×HCID 121909884,4-Dimethoxytetrahydro-2H-pyran-3-ol

Product 1

HCID 579387433-Ethoxy-4,4-dimethoxytetrahydro-2H-pyranYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4,4-dimethoxytetrahydro-2H-pyran-3-ol (2.0 g, 12 mmol) in THF (20 mL) cooled in an ice bath was slowly added sodium hydride (0.60 g, 15 mmol) and the resulting slurry was stirred for 1 h. Iodoethane (1.5 mL, 19 mmol) was added and the mixture was stirred at room temperature overnight. More sodium hydride (0.6 g) and iodoethane (3 mL) were added and stirring was continued another overnight. The reaction was quenched with water. The resulting solution was extracted with EtOAc twice and ether twice. The combined extracts were dried, concentrated and purified on silica gel (20% EtOAc/hexanes) to give 2.1 g (90%) of desired product. 1H NMR (CDCl3) δ 3.32-4.00 (7H, m), 3.30 (3H, s), 3.20 (3H, s), 2.05-1.70 (2H, m), 1.25-1.22 (3H, m).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. stirringstirring
  3. waitwas continued another overnight
  4. customThe reaction was quenched with water
  5. extractionThe resulting solution was extracted with EtOAc twice
  6. customThe combined extracts were dried
  7. concentrationconcentrated
  8. custompurified on silica gel (20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7bedb17697c24267b2c282eb01738855
Source dataset
uspto-grants-2013_10
Patent number
US08563582B2

Reaction notes

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