Iodoethane → 8-Ethoxy-1,4-dioxaspiro[4.5]decane

HRID 1947962Notes

Reaction equation

HRID 1947962 reaction equation
[H-].[Na+].[O:3]1[C:7]2([CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]2)[O:6][CH2:5][CH2:4]1.[CH2:14](I)[CH3:15]>C1COCC1>[CH2:14]([O:13][CH:10]1[CH2:11][CH2:12][C:7]2([O:6][CH2:5][CH2:4][O:3]2)[CH2:8][CH2:9]1)[CH3:15]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 5673521,4-Dioxaspiro(4.5)decan-8-ol

Product 1

HCID 5673588-Ethoxy-1,4-dioxaspiro[4.5]decaneYield 55.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (506 mg, 12.65 mmol) was added to a solution of 1,4-Dioxa-spiro[4.5]decan-8-ol (2 gm, 12.65 mmol) in dry THF (20 mL) at 0° C. After 15 minutes, ethyl iodide (2 gm, 12.65 mmol) was added and the mixture was allowed to stir at RT overnight. After removing the THF under reduced pressure, the mixture was poured into ice cold water and extracted into ethyl acetate. The crude product was purified by flash column chromatography (EtOAc:Hexane 5:95) to isolate the title compound (1.3 gm, 55%). 1H NMR (CDCl3, 500 MHz): δ 1.2 (t, 3H, J=7), 1.45-1.92 (m, 8H), 3.4 (m, 1H), 3.45 (m, 2H), 3.98 (m, 4H).

Workup

  1. customAfter removing the THF under reduced pressure
  2. additionthe mixture was poured into ice cold water
  3. extractionextracted into ethyl acetate
  4. customThe crude product was purified by flash column chromatography (EtOAc:Hexane 5:95)

Sources & evidence

ORD record
ord-3cd1ad02502040dea7a54b5425ebf52f
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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