1,4-Dioxaspiro[4.5]decan-8-one → 8-Benzyl-1,4-dioxaspiro[4.5]decan-8-ol

HRID 270026Notes

Reaction equation

HRID 270026 reaction equation
[CH2:1]([Mg]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10]1[O:20][C:13]2([CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH2:14]2)[O:12][CH2:11]1>C1COCC1>[CH2:1]([C:16]1([OH:19])[CH2:17][CH2:18][C:13]2([O:20][CH2:10][CH2:11][O:12]2)[CH2:14][CH2:15]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 178418336HCID 178418336, compound

Product 1

HCID 221798308-Benzyl-1,4-dioxaspiro[4.5]decan-8-olYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 0° C. solution of 2M benzylmagnesium chloride in THF (20 mL) was treated with a solution of 1,4-cyclohexanedione mono-ethylene ketal (6.24 g, 40 mmol) in THF (50 mL), warmed to room temperature, stirred overnight, quenched with saturated NH4Cl (100 mL), and extracted with ethyl acetate (3×100 mL). The combined extracts were washed with water and brine, dried (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 6:1 hexanes/ethyl acetate to provide the desired product (8.08 g, 81%). MS (CI) m/e 231(M−18), 249 (M+H), 266.2 (M+18)+.

Workup

  1. customquenched with saturated NH4Cl (100 mL)
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash column chromatography on silica gel with 6:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-a769667b99c14a30ac18f08da6c5c5be
Source dataset
uspto-grants-2008_11
Patent number
US07449485B2

Reaction notes

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