1,4-Dioxaspiro[4.5]decan-8-one → 8-(4-Fluorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol

HRID 2364102Notes

Reaction equation

HRID 2364102 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([Mg]Br)=[CH:15][CH:14]=1>C1COCC1>[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:8]2([OH:11])[CH2:7][CH2:6][C:5]3([O:4][CH2:3][CH2:2][O:1]3)[CH2:10][CH2:9]2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 178418676HCID 178418676, compound

Product 1

HCID 152326818-(4-Fluorophenyl)-1,4-dioxaspiro[4.5]decan-8-olYield 40.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1,4-dioxaspiro[4.5]decan-8-one (3.00 g, 19.2 mmol) in THF (80 mL) was dropwise added (4-fluorophenyl) magnesium bromide (1.0 M in THF, 28.8 mL, 28.8 mmol) at 0° C. over 15 min. The mixture was stirred at 0° C. for 30 min, and then quenched with aqueous NH4Cl (100 mL). The layers were separated and the aqueous layer was extracted with EtOAc (30 mL). The combined organic layers were washed with brine (15 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (Purif, silica gel, 80:20 hexane/EtOAc to 50:50 hexane/EtOAc) to give title compound (1.96 g, 40%) as a colorless solid:

Workup

  1. customat 0° C.
  2. customover 15 min
  3. customquenched with aqueous NH4Cl (100 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with EtOAc (30 mL)
  6. washThe combined organic layers were washed with brine (15 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography (Purif, silica gel, 80:20 hexane/EtOAc to 50:50 hexane/EtOAc)

Sources & evidence

ORD record
ord-3668baa10a614e5893944b018b0c748a
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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