Ethyl bromoacetate → Ethyl 3-oxo-4-morpholineacetate

HRID 1786182Notes

Reaction equation

HRID 1786182 reaction equation
[O:1]=[C:2]1[CH2:7][O:6][CH2:5][CH2:4][NH:3]1.[H-].[Na+].Br[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]>CN(C=O)C>[CH2:15]([O:14][C:12](=[O:13])[CH2:11][N:3]1[CH2:4][CH2:5][O:6][CH2:7][C:2]1=[O:1])[CH3:16]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 669533-Morpholinone

Product 1

HCID 67549692Ethyl 3-oxo-4-morpholineacetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3-oxo-morpholine (6.5 g, 4 mmol) (Willey, Alan David; Kott, Kevin Lee; Miracle, Gregory Scot; Gosselink, Eugene Paul; Burckett-St. Laurent, James Charles Theophile Roger. Bleaching compositions containing bleach activators having alpha-modified lactam leaving-groups. PCT Int. Appl. (1996), WO 9622350 A1) in DMF (45 mL) was treated at rt in 3 portions with sodium hydride (3.34 g, 60% dispersion in mineral oil, 84 mmol). After 30 min a solution of ethyl bromoacetate (11.8 g, 71 mmol) in DMF (20 mL) was added dropwise. After 3 h the solvent was evaporated, the residue was taken up with ethyl acetate and washed with water. The organic phase was dried over sodium sulfate, concentrated and chromatographed (SiO2, dichloromethane:methanol=1000:0 to 995:5). The title compound was obtained as a light yellow oil (3.34 g, 28%). 1H-NMR (300 MHz, DMSO): δ=1.19 (t, J=7 Hz, 3H), 3.40 (mc, 2H), 3.85 (mc, 2H), 4.05-4.28 (m, 6H)

Workup

  1. customAfter 3 h the solvent was evaporated
  2. washwashed with water
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated
  5. customchromatographed (SiO2, dichloromethane:methanol=1000:0 to 995:5)

Sources & evidence

ORD record
ord-e61829b865e54994a2c8febfc8aed225
Source dataset
uspto-grants-2009_03
Patent number
US07507729B2

Reaction notes

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