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

HRID 1436756Notes

Reaction equation

HRID 1436756 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 6340IodoethaneHCID 24758Sodium hydride2×HCID 121909884,4-Dimethoxytetrahydro-2H-pyran-3-ol

Product 1

HCID 579387433-Ethoxy-4,4-dimethoxytetrahydro-2H-pyranYield 90%

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

Sources & evidence

ORD record
ord-e9f3b20ac27b4b7a9fd8bfad71d72f9a
Source dataset
uspto-grants-2009_11
Patent number
US07618970B2

Reaction notes

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