Sodium hydride → HCID 86671481, compound

HRID 1530708Notes

Reaction equation

HRID 1530708 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH:5]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[H-].[Na+].C1C(=O)N([Br:25])C(=O)C1>C1COCC1>[CH2:1]([O:3][C:4](=[O:15])[C:5]([Br:25])([CH2:11][CH:12]([CH3:13])[CH3:14])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 25047Diethyl isobutylmalonateHCID 67184N-bromobutanimide

Product 1

HCID 86671481HCID 86671481, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cooled solution of 2-isobutylmalonic acid diethyl ester (3.21 g, 14.8 mmol) in THF (50 mL) was added portionwise sodium hydride (1.19 g, 60% in oil, 29.7 mmol). The mixture was stirred in the ice bath for 15 min, and then at RT for 15 min. The suspension was re-cooled in the ice bath and NBS (2.9 g, 16.3 mmol) was added over 5 min. The mixture was stirred in the ice bath for 10 min, and then at RT for 30 min. The reaction mixture was filtered through Celite® and the filtrate concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 2-6% EtOAc in cyclohexane) affording the title compound as a colourless oil (3.828 g, 88%). 1H NMR (CDCl3, 300 MHz): δ 4.27 & 4.26 (4H, 2 q, J=7.1 Hz), 2.26 (2H, d, J=6.2 Hz) 1.95 (1H, nonet, J=6.5 Hz), 1.29 (6H, t, J=7.1 Hz), 0.94 (6H, d, J=6.7 Hz).

Workup

  1. additionwas added over 5 min
  2. waitat RT for 30 min
  3. filtrationThe reaction mixture was filtered through Celite®
  4. concentrationthe filtrate concentrated in vacuo
  5. customThe resulting residue was purified by column chromatography (Si-PCC, gradient 2-6% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-8a9df85fa7fc43459d23499e55b94431
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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