Iodoethane → 3-Ethoxy-2,2-dimethylpropionic acid methyl ester

HRID 1802421Notes

Reaction equation

HRID 1802421 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:11])[C:6]([CH3:10])([CH3:9])[CH2:7][OH:8].I[CH2:13][CH3:14]>CN(C=O)C>[CH3:3][O:4][C:5](=[O:11])[C:6]([CH3:10])([CH3:9])[CH2:7][O:8][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 84152Methyl 3-hydroxypivalate

Product 1

HCID 592680143-Ethoxy-2,2-dimethylpropionic acid methyl esterYield 99.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

60% Sodium hydride in mineral oil (1.6 g, 39.2 mmol) is added to a solution of 3-hydroxy-2,2-dimethyl-propionic acid methyl ester (2.0 mL, 15.7 mmol) in 30.0 mL of DMF, followed by the addition of iodoethane (3.1 mL, 39.2 mmol) and the reaction mixture is stirred at room temperature for 1 hour. After this time, the reaction mixture is quenched with saturated NH4Cl aqueous solution and then extracted with dichloromethane twice. The organics are combined and washed with water twice then brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield 2.512 g of the title compound. Yield: quantitative; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.16 (3H, t, J=8.0 Hz), 1.20 (6H, s), 3.41 (2H, s), 3.48 (2H, q, J=8.0 Hz), 3.70 (3H, s).

Workup

  1. customAfter this time, the reaction mixture is quenched with saturated NH4Cl aqueous solution
  2. extractionextracted with dichloromethane twice
  3. washwashed with water twice
  4. dry with materialbrine, dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-32722e6a0f824b3a895da28e4ee3bcdb
Source dataset
uspto-grants-2013_01
Patent number
US08349871B2

Reaction notes

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