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

HRID 1858929Notes

Reaction equation

HRID 1858929 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>C1COCC1>[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 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 1,4-cyclohexanedione monoethylene ketal (31.2 g, 200 mmole) in dry THF (250 ml) was added to a solution of 4-fluorophenylmagnesium bromide in dry THF at -60° C. The mixture was allowed to warm to 25° C. and quenched with saturated NH4Cl solution and extracted with ether. The extracts were dried with Na2SO4 and the solvent removed in vacuo. The residue was crystallized from hexane to give the product (89%, mp:133-135° C.). Calc'd for C14H17FO3 : C, 66.66%; H, 6.80%. Found: C, 66.54%; H, 7.12%.

Workup

  1. customquenched with saturated NH4Cl solution
  2. extractionextracted with ether
  3. dry with materialThe extracts were dried with Na2SO4
  4. customthe solvent removed in vacuo
  5. customThe residue was crystallized from hexane

Sources & evidence

ORD record
ord-6144bdbb5b30403082b1ce36b5e4661f
Source dataset
uspto-grants-2000_11
Patent number
US06153611

Reaction notes

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