Water → 1-(1,4-Dioxaspiro[4.5]decan-8-yl)propan-1-one

HRID 626180Notes

Reaction equation

HRID 626180 reaction equation
CON(C)[C:4]([CH:6]1[CH2:15][CH2:14][C:9]2([O:13][CH2:12][CH2:11][O:10]2)[CH2:8][CH2:7]1)=[O:5].[CH3:17][CH2:18][Mg+].[Br-].O>CCOCC>[O:10]1[C:9]2([CH2:8][CH2:7][CH:6]([C:4](=[O:5])[CH2:17][CH3:18])[CH2:15][CH2:14]2)[O:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 962WaterHCID 15643268N-methoxy-N-methyl-1,4-Dioxaspiro[4.5]decane-8-carboxamideHCID 178461630HCID 178461630, compound

Product 1

HCID 896574821-(1,4-Dioxaspiro[4.5]decan-8-yl)propan-1-oneYield 30.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of N-methoxy-N-methyl-1,4-dioxaspiro[4.5]decane-8-carboxamide (1 g, 0.0043 mol) in anhydrous Et2O (20 mL) was added EtMgBr (9 g, 0.043 mol). The reaction mixture was refluxed overnight, and then 200 mL water was added. The mixture was extracted with ethyl acetate. The extract was concentrated and purified by silica gel column chromatography (CH2Cl2:MeOH=150:1) to give the desired product (0.259 g, 26% yield).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. extractionThe mixture was extracted with ethyl acetate
  3. concentrationThe extract was concentrated
  4. custompurified by silica gel column chromatography (CH2Cl2:MeOH=150:1)

Sources & evidence

ORD record
ord-6c3cc8e44468453893a45c54db5eebf1
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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