Sodium hydride → HCID 12491978, compound

HRID 1530687Notes

Reaction equation

HRID 1530687 reaction equation
[C:1]1([CH:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].C1C(=O)N([Br:27])C(=O)C1>C1COCC1>[CH2:16]([O:15][C:13](=[O:14])[C:7]([Br:27])([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:17]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 66514Diethyl phenylmalonateHCID 67184N-bromobutanimide

Product 1

HCID 12491978HCID 12491978, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cooled solution of diethyl phenylmalonate (3.0 g, 12.7 mmol) in THF (90 mL) was added portionwise sodium hydride (1.015 g, 60% in oil, 25.4 mmol). The mixture was stirred in the ice bath for 30 min and NBS (2.486 g, 14 mmol) was added. The mixture was stirred in the ice bath for 10 min, and then at RT for 20 min. The reaction mixture was filtered through Celite® and the filtrate concentrated in vacuo. The residue was dissolved in DCM, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 2-8% EtOAc in cyclohexane) affording the title compound as a colourless oil (3.418 g, 85%). 1H NMR (CDCl3, 300 MHz): δ 7.60-7.56 (2H, m), 7.39-7.32 (3H, m), 4.33 (2H, q, J=7.1 Hz), 4.32 (2H, q, J=7.1 Hz), 1.30 (6H, d, J=7.1 Hz).

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. concentrationthe filtrate concentrated in vacuo
  3. dissolutionThe residue was dissolved in DCM
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by column chromatography (Si-PCC, gradient 2-8% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-0e691d663b6b465c83733c3ebe87e6eb
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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