Ethylene Glycol → 2-(2-Isopropyl-1,3-dioxolan-2-yl)acetonitrile

HRID 871475Notes

Reaction equation

HRID 871475 reaction equation
[CH3:1][CH:2]([CH3:8])[C:3](=[O:7])[CH2:4][C:5]#[N:6].[CH2:9](O)[CH2:10][OH:11].Cl[Si](C)(C)C.C(=O)(O)[O-].[Na+]>ClCCl>[CH:2]([C:3]1([CH2:4][C:5]#[N:6])[O:11][CH2:10][CH2:9][O:7]1)([CH3:8])[CH3:1]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 6397ChlorotrimethylsilaneHCID 516892Sodium BicarbonateHCID 101299214-Methyl-3-oxopentanenitrile

Product 1

HCID 668767212-(2-Isopropyl-1,3-dioxolan-2-yl)acetonitrileYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

4-Methyl-3-oxopentanenitrile was added to a mixture of ethylene glycol (4.7 mL, 84 mmol) and chlorotrimethylsilane (10.6 mL, 84 mmol) in anhydrous dichloromethane (50 mL). The mixture was stirred at 40° C. overnight. After cooling to room temperature a solution of 5% sodium bicarbonate (50 mL) was added, the layer were separated and the water phase back extracted three times with diethyl ether. The organics were combined, dried (MgSO4), filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane/ethyl acetate 8:2) to afford 2-(2-isopropyl-1,3-dioxolan-2-yl)acetonitrile (3.38 g, 78%) as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 4.21-4.16 (m, 2H), 4.07-3.99 (m, 2H), 2.69 (s, 2H), 2.08-2.01 (m, 1H), 0.96 (d, 6H).

Workup

  1. additionwas added
  2. customthe layer were separated
  3. extractionthe water phase back extracted three times with diethyl ether
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel chromatography (hexane/ethyl acetate 8:2)

Sources & evidence

ORD record
ord-a8bbbd52590c42eab36dcfe8d298fb5f
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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