Sodium Methoxide → 2-Methoxy-1-(1,4-dioxaspiro[4.5]decan-8-yl)ethanol

HRID 1896832Notes

Reaction equation

HRID 1896832 reaction equation
[O:1]1[CH2:3][CH:2]1[CH:4]1[CH2:13][CH2:12][C:7]2([O:11][CH2:10][CH2:9][O:8]2)[CH2:6][CH2:5]1.[CH3:14][O-:15].[Na+]>C(Cl)Cl>[CH3:14][O:15][CH2:3][CH:2]([CH:4]1[CH2:13][CH2:12][C:7]2([O:11][CH2:10][CH2:9][O:8]2)[CH2:6][CH2:5]1)[OH:1]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 585624888-(Oxiran-2-yl)-1,4-dioxaspiro[4.5]decane

Product 1

HCID 585624972-Methoxy-1-(1,4-dioxaspiro[4.5]decan-8-yl)ethanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8-(oxiran-2-yl)-1,4-dioxaspiro[4.5]decane (202 mg, 1.10 mmol), prepared in the previous step, in DCM (20 mL) was dissolved in sodium methoxide solution (10 mL, 5 mmol, 0.5 M). The mixture was stirred, heating to reflux under argon overnight and then cooled to ambient temperature and concentrated in vacuo. After addition of saturated ammonium chloride solution and extraction with ethyl acetate, the organic layers were concentrated in vacuo and the residue was purified by flash chromatography (silica gel, 0-50% ether) to afford the product.

Workup

  1. temperatureheating
  2. temperatureto reflux under argon overnight
  3. concentrationconcentrated in vacuo
  4. additionAfter addition of saturated ammonium chloride solution and extraction with ethyl acetate
  5. concentrationthe organic layers were concentrated in vacuo
  6. customthe residue was purified by flash chromatography (silica gel, 0-50% ether)
  7. customto afford the product

Sources & evidence

ORD record
ord-e5b1f78e387b4176bd10f9fc7660a0ef
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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