Diethyl Ether → (8-Hydroxy-1,4-dioxa-spiro[4.5]dec-8-yl)-acetaldehyde

HRID 1615113Notes

Reaction equation

HRID 1615113 reaction equation
[CH2:1]([C:4]1([OH:14])[CH2:13][CH2:12][C:7]2([O:11][CH2:10][CH2:9][O:8]2)[CH2:6][CH2:5]1)[CH:2]=C.C([O:17]CC)C.[O-]S([O-])(=S)=O.[Na+].[Na+]>O=[Os](=O)(=O)=O.O>[OH:14][C:4]1([CH2:1][CH:2]=[O:17])[CH2:13][CH2:12][C:7]2([O:11][CH2:10][CH2:9][O:8]2)[CH2:6][CH2:5]1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 24477Sodium ThiosulfateHCID 584813948-Allyl-1,4-dioxa-spiro[4.5]decan-8-ol

Product 1

HCID 57815370(8-Hydroxy-1,4-dioxa-spiro[4.5]dec-8-yl)-acetaldehyde

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

NalO4 (18.13 g) followed by OsO4 (4% in water, 0.96 mL) is added to a mixture of 8-allyl-1,4-dioxa-spiro[4.5]decan-8-ol (12.59 g), diethyl ether (65 ml), and water (85 mL) at room temperature. The mixture is vigorously stirred at room temperature overnight, before aqueous Na2S2O3 solution (50 mL) is added and stirring is continued for another 45 min. The combined organic phases are washed with water, dried (MgSO4), and concentrated. The crude product is used without further purification. Yield: 2.68 g (ca. 70% pure); Mass spectrum (ESI+): m/z=201 [M+H]+.

Workup

  1. additionis added
  2. washThe combined organic phases are washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude product is used without further purification

Sources & evidence

ORD record
ord-84f689147826455786853cfcebfb66cd
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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