Hydrochloric Acid → HCID 59253251, compound

HRID 386887Notes

Reaction equation

HRID 386887 reaction equation
CO[C:3](=[O:13])[C:4]([CH3:12])([CH3:11])[CH2:5][O:6][CH2:7][CH2:8][O:9][CH3:10].[C:14](#[N:16])[CH3:15].[H-].[Na+].Cl>C1(C)C=CC=CC=1>[CH3:10][O:9][CH2:8][CH2:7][O:6][CH2:5][C:4]([CH3:11])([CH3:12])[C:3](=[O:13])[CH2:15][C:14]#[N:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 59253200HCID 59253200, compound

Product 1

HCID 59253251HCID 59253251, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 3-(2-methoxy-ethoxy)-2,2-dimethyl-propionic acid methyl ester (3.08 g, 16.21 mmol) and acetonitrile (1.19 mL, 22.69 mmol) in toluene (6 mL) is added dropwise to the refluxing suspension of 60% sodium hydride in mineral oil (907.6 mg, 22.69 mmol) in toluene (18 mL). After the addition, the reaction mixture is stirred at reflux for 3 h. After this time, the reaction mixture is cooled to room temperature and the aqueous layer is neutralized to pH˜7 by adding 1M aqueous HCl solution. The aqueous layer is extracted with ethyl acetate 3 times. The organic layers are combined, washed with brine, dried over Na2SO4 and filtered. The filtrate is concentrated under reduced pressure to yield the title compound. Yield: 94.2%. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.20 (6H, s), 3.38 (3H, s), 3.47 (2H, s), 3.50-3.55 (2H, m), 3.57-3.62 (2H, m), 3.80 (2H, s).

Workup

  1. additionAfter the addition
  2. temperatureat reflux for 3 h
  3. extractionThe aqueous layer is extracted with ethyl acetate 3 times
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-ae1acbb3585e4094b1107c4034769d69
Source dataset
uspto-grants-2013_02
Patent number
US08372874B2

Reaction notes

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