1,4-Dioxane → 1-(Methoxymethyl)-3-oxocyclobutane-1-carbonitrile

HRID 1966147Notes

Reaction equation

HRID 1966147 reaction equation
[O:1]1CCOCC1.[CH3:7][O:8][CH2:9][C:10]1([C:15]#[N:16])[CH2:13][C:12](=C)[CH2:11]1.I([O-])(=O)(=O)=O.[Na+]>O.[Os](=O)(=O)(=O)=O>[CH3:7][O:8][CH2:9][C:10]1([C:15]#[N:16])[CH2:13][C:12](=[O:1])[CH2:11]1

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 23667635Sodium periodateHCID 668243071-(Methoxymethyl)-3-methylidenecyclobutane-1-carbonitrile

Product 1

HCID 668243301-(Methoxymethyl)-3-oxocyclobutane-1-carbonitrile

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×

Procedure

A mixture of water (2 mL, 0.1 mol) and 1,4-dioxane (7 mL, 0.08 mol), 1-(methoxymethyl)-3-methylenecyclobutanecarbonitrile (0.294 g, 0.00214 mol), and 0.2 M of osmium tetraoxide in water (0.04 mL) was stirred for 5 min, during which time the mixture became brown. While the temperature was maintained at room temperature, sodium periodate (0.963 g, 0.00450 mol) was added in portions over a period of 30 min. The mixture was stirred overnight. The mixture was extracted with EtOAc and the combined organic layers were dried over MgSO4. After removal of the solvents, the crude product was used directly in next step (298 mg, 99.92%). 1H NMR (400 MHz, CDCl3): 3.70 (2H, s), 3.68 (3H, s), 3.58 (2H, m), 3.38 (2H, m) ppm.

Workup

  1. stirringThe mixture was stirred overnight
  2. extractionThe mixture was extracted with EtOAc
  3. dry with materialthe combined organic layers were dried over MgSO4
  4. customAfter removal of the solvents

Sources & evidence

ORD record
ord-3cade7c4406146558fa35bab0dc1e627
Source dataset
uspto-grants-2013_04
Patent number
US08420629B2

Reaction notes

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