Water → 3-(2-Chloroethoxy)-2,2-dimethylpropanenitrile

HRID 1365738Notes

Reaction equation

HRID 1365738 reaction equation
[Li+].CC([N-]C(C)C)C.[C:9](#[N:13])[CH:10]([CH3:12])[CH3:11].[Cl:14][CH2:15][CH2:16][O:17][CH2:18]Cl.O>C1COCC1.CCOCC>[Cl:14][CH2:15][CH2:16][O:17][CH2:18][C:10]([CH3:12])([CH3:11])[C:9]#[N:13]

Participants

7

Reactant 4

HCID 962WaterHCID 6559IsobutyronitrileHCID 2724682Lithium diisopropylamideHCID 102908101-Chloro-2-(chloromethoxy)ethane

Product 1

HCID 553031313-(2-Chloroethoxy)-2,2-dimethylpropanenitrileYield 101.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of LDA (0.14 mol) in 100 mL THF at −30 C under N2 was added drop-wise isobutyronitrile (9.7 g, 0.14 mol) in 40 mL THF over 20 min. After 20 min, a solution of 1-chloro-2-(chloromethoxy)ethane (18.1 g, 0.14 mol) in 50 mL THF was added drop-wise and the temperature was allowed to gradually rise to room temperature and stirred for 5 h. This was treated with 200 mL of water and Et2O and the layers separated. The aqueous layer was extracted further with Et2O. The combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated to leave 23 g of crude product as a yellow oil. This was purified by silica chromatography using 9:1 hexanes/CH2Cl2 to 4:1 hexanes/CH2Cl2 as eluants. This yielded 7.4 g (32%) of the title compound as an oil. 1H NMR (300 MHz, CDCl3) δ: 1.33 (s, 6H), 3.43 (s, 2H), 3.61 (t, J=5.7 Hz, 2H), 3.77 (t, J=5.9 Hz, 2H). LC/MS (M+H): 162.

Workup

  1. customto gradually rise to room temperature
  2. customthe layers separated
  3. extractionThe aqueous layer was extracted further with Et2O
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f499cd8b98a745aabb73916bf5dc427e
Source dataset
uspto-grants-2011_02
Patent number
US07893055B2

Reaction notes

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