Sodium hydride → HCID 68312962, compound

HRID 1530693Notes

Reaction equation

HRID 1530693 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH:5]([CH2:11][CH:12]1[CH2:14][CH2:13]1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[H-].[Na+].C1C(=O)N([Br:25])C(=O)C1>C1COCC1>[CH2:9]([O:8][C:6](=[O:7])[C:5]([Br:25])([CH2:11][CH:12]1[CH2:13][CH2:14]1)[C:4]([O:3][CH2:1][CH3:2])=[O:15])[CH3:10]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 67184N-bromobutanimideHCID 11564752HCID 11564752, compound

Product 1

HCID 68312962HCID 68312962, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cooled solution of 2-cyclopropylmethylmalonic acid diethyl ester (1.3 g, 6.067 mmol) in THF (45 mL) was added, portionwise, sodium hydride (0.485 g, 60% in oil, 12.13 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 (1.19 g, 6.67 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 2-8% EtOAc in cyclohexane) affording the title compound as a colourless oil (1.55 g, 87%). 1H NMR (CDCl3, 300 MHz): δ 4.33-4.22 (4H, m), 2.24 (2H, d, J=6.6 Hz) 1.30 (6H, d, J=7.1 Hz) 1.01-0.88 (1H, m), 0.54-0.48 (2H, m), 0.17-0.12 (2H, m).

Workup

  1. additionwas added
  2. additionwas added over 5 min
  3. waitat RT for 30 min
  4. filtrationThe reaction mixture was filtered through Celite®
  5. concentrationthe filtrate concentrated in vacuo
  6. customThe resulting residue was purified by column chromatography (Si-PCC, gradient 2-8% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-15afb9d2bf7c462f9bf440906cea3636
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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