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

HRID 1637083Notes

Reaction equation

HRID 1637083 reaction equation
[CH2:1]1[O:11][C:4]2([CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]2)[O:3][CH2:2]1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([Mg]Br)=[CH:15][CH:14]=1>C(OCC)C>[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:7]2([OH:10])[CH2:6][CH2:5][C:4]3([O:3][CH2:2][CH2:1][O:11]3)[CH2:9][CH2:8]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 95%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1,4-cyclohexanedione mono-ethylene ketal (25 g, 0.16 mol) in diethylether (750 ml), cooled to -78° C. was added 4-fluorophenyl magnesium bromide (1 M in tetrahydrofuran, 190 ml, 0.19 mol) dropwise. The reaction mixture was warmed to room temperature, quenched with water and extracted twice with ethyl acetate. Washing with brine, drying and solvent evaporation gave 8-(4-fluorophenyl)-1,4-dioxa-spiro[4.5]decan-8-ol (38 g, 95%).

Workup

  1. customquenched with water
  2. extractionextracted twice with ethyl acetate
  3. washWashing with brine
  4. customdrying
  5. customsolvent evaporation

Sources & evidence

ORD record
ord-8a8a979a0f7f44b78038c6e04c0425d0
Source dataset
uspto-grants-2000_03
Patent number
US06037354

Reaction notes

Loading…