Ammonium Chloride → 8-Methyl-1,4-dioxaspiro(4.5)decan-8-ol

HRID 509281Notes

Reaction equation

HRID 509281 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.[CH3:12][Mg]Cl.[Cl-].[NH4+]>C1COCC1>[CH3:12][C:7]1([OH:10])[CH2:6][CH2:5][C:4]2([O:3][CH2:2][CH2:1][O:11]2)[CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 178418332HCID 178418332, compound

Product 1

HCID 187130758-Methyl-1,4-dioxaspiro(4.5)decan-8-olYield 59.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,4-cyclohexandione mono-ethylene ketal (1.0 g, 6.4 mmol) was dissolved in THF (30 ml), followed by addition of MeMgCl (3.0M solution in THF, 2.6 ml, 7.7 mmol) at 0° C., and then the resulting mixture was stirred at room temperature under nitrogen stream for 3 hours. A saturated aqueous ammonium chloride solution was added to the resulting reaction liquid, followed by extraction with MC (50 ml×2). The organic layer was dried over anhydrous sodium sulfate, followed by filtration and concentration, and then the residue thus obtained was subjected to MPLC (50% EtOAc/Hexanes), to obtain 654 mg of white solid (59%).

Workup

  1. extractionfollowed by extraction with MC (50 ml×2)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfollowed by filtration and concentration
  4. customthe residue thus obtained

Sources & evidence

ORD record
ord-6e346a96b752436cb79c9efbd46cfbf8
Source dataset
uspto-grants-2015_08
Patent number
US09096571B2

Reaction notes

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