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

HRID 631430Notes

Reaction equation

HRID 631430 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-0e2abf1c316a4bcab5e0bf708cd5d47f
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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