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

HRID 714254Notes

Reaction equation

HRID 714254 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. Next, the stirring was stopped and the mixture was added to EtOAc and washed with water, aq. Na2S2O3, and brine. The resulting material was dried over Na2SO4 and evaporated to give an oily residue.

Workup

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

Sources & evidence

ORD record
ord-bd2a8c2a1c564b498666b0291e34d45c
Source dataset
uspto-grants-2015_11
Patent number
US09187437B2

Reaction notes

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