Ethyl chloroacetate → HCID 67323672, compound

HRID 1029036Notes

Reaction equation

HRID 1029036 reaction equation
[CH3:1][C:2](C)([O-])C.[K+].[Br:7][C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=1[NH:15][CH2:16][CH2:17][OH:18].ClCC(OCC)=[O:22]>C1COCC1>[Br:7][C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=1[N:15]1[CH2:2][CH2:1][O:18][CH2:17][C:16]1=[O:22]

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetate2×HCID 23665647Potassium tert-butoxide2×HCID 66816832HCID 66816832, compound

Product 1

HCID 67323672HCID 67323672, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of THF were added successively potassium tert-butoxide (572 mg, 5.10 mmol), 2-(2-bromo-3-methylphenylamino)ethanol (1151 mg, 5 mmol) and ethyl 2-chloroacetate (0.565 mL, 5.30 mmol). The resulting suspension was stirred for 16 h at RT. Additional KOtBu (200 mg) and ethyl 2-chloroacetate (0.15 ml) were added and the reaction mixture was heated to 36° C. for additional 2 h. The reaction was quenched with water and 1M HCl, followed by addition of EtOAc. The organic phase was separated, washed with brine and dried over MgSO4. The solvent was removed under reduced pressure and the remaining residue was purified by flash chromatography (5-70% EtOAc/hexanes). 4-(2-Bromo-3-methylphenyl)morpholin-3-one was obtained as a light-yellow powder.

Workup

  1. temperaturethe reaction mixture was heated to 36° C. for additional 2 h
  2. customThe reaction was quenched with water and 1M HCl
  3. additionfollowed by addition of EtOAc
  4. customThe organic phase was separated
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. customThe solvent was removed under reduced pressure
  8. customthe remaining residue was purified by flash chromatography (5-70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-5df5860fc0374649bcbe934be0aabebe
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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