Ethyl bromoacetate → HCID 86754777, compound

HRID 322499Notes

Reaction equation

HRID 322499 reaction equation
[O:1]=[C:2]1[CH:6]([CH2:7][CH2:8][CH:9]2[O:14][CH2:13][CH2:12][O:11][CH2:10]2)[CH2:5][CH2:4][NH:3]1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>C1COCC1>[O:1]=[C:2]1[CH:6]([CH2:7][CH2:8][CH:9]2[O:14][CH2:13][CH2:12][O:11][CH2:10]2)[CH2:5][CH2:4][N:3]1[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 70061850HCID 70061850, compound

Product 1

HCID 86754777HCID 86754777, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a rapidly stirred solution of 2-3 (0.86 g, 4.3 mmol) and THF (25 mL) at −78° C. was added NaN(TMS)2 (5.2 mL, 5.2 mmol, 1.0 M in THF). After 20 min, ethyl bromoacetate (0.58 mL, 5.2 mmol) was added followed by removal of the cooling bath. After 1 h, the reaction mixture was diluted with EtOAc and then washed with H2O, sat. NaHCO3 and brine, dried (MgSO4), and concentrated to give 2-4 as a yellow oil.

Workup

  1. customfollowed by removal of the cooling bath
  2. waitAfter 1 h
  3. additionthe reaction mixture was diluted with EtOAc
  4. washwashed with H2O, sat. NaHCO3 and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-933cdc11f8914b989e7d03b51e731aa8
Source dataset
uspto-grants-2001_04
Patent number
US06211184B1

Reaction notes

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