Ethyl Acetate → 2-(6-Phenyl-1,4-dioxaspiro[4.5]decan-6-yl)acetaldehyde

HRID 71250Notes

Reaction equation

HRID 71250 reaction equation
[CH2:1]([C:4]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:13][CH2:12][CH2:11][CH2:10][C:5]21[O:9][CH2:8][CH2:7][O:6]2)[CH:2]=C.I([O-])(=O)(=O)=[O:21].[Na+].CCOC(C)=O>C1COCC1.O.CC(O)(C)C.O=[Os](=O)(=O)=O>[C:14]1([C:4]2([CH2:1][CH:2]=[O:21])[CH2:13][CH2:12][CH2:11][CH2:10][C:5]32[O:6][CH2:7][CH2:8][O:9]3)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 3

HCID 8857Ethyl AcetateHCID 23667635Sodium periodateHCID 666925036-Allyl-6-phenyl-1,4-dioxaspiro[4.5]decane

Product 1

HCID 866882042-(6-Phenyl-1,4-dioxaspiro[4.5]decan-6-yl)acetaldehyde

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-allyl-6-phenyl-1,4-dioxaspiro[4.5]decane (444 mg, 1.719 mmol) in THF (5 mL) was added a solution of sodium periodate (441 mg, 2.062 mmol) in water (5.00 mL), and 0.175 ml of 2.5% OsO4 in t-BuOH, and the mixture was stirred for 3 hrs. At the end of the stirring it was added to EtOAc and washed with water, aq. Na2S2O3 and brine. It was dried over Na2SO4 and evaporated to give an oily residue.

Workup

  1. washwashed with water, aq. Na2S2O3 and brine
  2. dry with materialIt was dried over Na2SO4
  3. customevaporated
  4. customto give an oily residue

Sources & evidence

ORD record
ord-3b1fe4abde134b58b1548abb75f42864
Source dataset
uspto-grants-2014_09
Patent number
US08822510B2

Reaction notes

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