Water → 3-(Dimethoxymethyl)-4,4-dimethoxybutanenitrile

HRID 1850670Notes

Reaction equation

HRID 1850670 reaction equation
[CH3:1][O:2][CH:3]([O:16][CH3:17])[CH:4]([CH:11]([O:14][CH3:15])[O:12][CH3:13])[CH2:5][CH2:6]S([O-])(=O)=O.C(OCC)(=O)C.O.CC#[N:27]>[C-]#N.C([N+](CC)(CC)CC)C>[CH3:1][O:2][CH:3]([O:16][CH3:17])[CH:4]([CH:11]([O:14][CH3:15])[O:12][CH3:13])[CH2:5][C:6]#[N:27]

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 86720913[2-(Dimethoxymethyl)-3,3-dimethoxypropyl]methanesulfonate

Product 1

HCID 867208913-(Dimethoxymethyl)-4,4-dimethoxybutanenitrile

Reagents, catalysts & solvents 1

HCID 3014735Tetraethylammonium cyanideCatalyst

Procedure

Tetraethylammonium cyanide (142.3 g, 910.8 mmol) was added portionwise over 10 minutes to a solution of [2-(dimethoxymethyl)-3,3-dimethoxypropyl]methanesulfonate (124 g, 455.4 mmol) in MeCN (1.24 L). The reaction mixture was stirred at room temperature for 72 h, then portioned between ethyl acetate (1.24 L) and water (1.24 L). The layers were separated and the organic layer was isolated, washed with brine. The organics were dried over MgSO4, filtered and evaporated to give 3-(dimethoxymethyl)-4,4-dimethoxybutanenitrile 11 as a dark brown oil (86.1 g).

Workup

  1. customThe layers were separated
  2. customthe organic layer was isolated
  3. washwashed with brine
  4. dry with materialThe organics were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-992c14a3fcdc498ca638097f7af61b79
Source dataset
uspto-grants-2015_02
Patent number
US08957078B2

Reaction notes

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