Sodium hydride → HCID 59253200, compound

HRID 386886Notes

Reaction equation

HRID 386886 reaction equation
[OH:1][CH2:2][C:3]([CH3:9])([CH3:8])[C:4]([O:6][CH3:7])=[O:5].[H-].[Na+].[CH3:12][O:13][CH2:14][CH2:15]Br>CN(C=O)C>[CH3:7][O:6][C:4](=[O:5])[C:3]([CH3:9])([CH3:8])[CH2:2][O:1][CH2:15][CH2:14][O:13][CH3:12]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 84152Methyl 3-hydroxypivalate

Product 1

HCID 59253200HCID 59253200, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 3-hydroxy-2,2-dimethyl-propionate (2.72 mL, 21.28 mmol) in 3 mL of DMF is added 60% sodium hydride in mineral oil (1.70 g, 42.56 mmol) in one portion, followed by the addition of 2-bromoethyl methyl ether (4.0 mL, 42.56 mmol). The reaction mixture is stirred at room temperature for 3 hs. After this time, the reaction mixture is quenched with saturated aqueous NH4Cl solution and the product is extracted with DCM twice. The organics are combined and washed with water 4 times then brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield the title compound. Yield: 76%; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.19 (6H, s), 3.36 (3H, s), 3.48 (2H, s), 3.48-3.52 (2H, m), 3.54-3.60 (2H, m), 3.67 (3H, s).

Workup

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

Sources & evidence

ORD record
ord-a6498b8fd963426dbcb9e97753ea214a
Source dataset
uspto-grants-2013_02
Patent number
US08372874B2

Reaction notes

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