Diethyl ethylmalonate → HCID 131733864, compound

HRID 708844Notes

Reaction equation

HRID 708844 reaction equation
[H-].[Na+].[CH2:3]([CH:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:4].F[C:17]1[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][C:18]=1[CH2:19][N:20]([CH3:31])[C:21](=[O:30])[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CS(C)=O>[CH2:23]([O:22][C:21]([N:20]([CH2:19][C:18]1[CH:32]=[C:33]([N+:36]([O-:38])=[O:37])[CH:34]=[CH:35][C:17]=1[C:5]([CH2:3][CH3:4])([C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH3:31])=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 8610Diethyl ethylmalonateHCID 24758Sodium hydrideHCID 118092892HCID 118092892, compound

Product 1

HCID 131733864HCID 131733864, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

To a flask with sodium hydride (207 mg, 8.64 mmol) was added DMSO (5 mL). The mixture was stirred at rt for 5 min. Diethyl 2-ethylmalonate (1626 mg, 8.64 mmol) in DMSO (5 mL) was added. After 20 min stirring, 13A (550 mg, 1.728 mmol) in DMSO (5 mL) was added. The reaction mixture was heated at 65° C. over night. The reaction was quenched with water, extracted with EtOAc. The organic layer was dried over sodium sulfate and concentrated. The crude product was purified by flash chromatography to give 13B (820 mg, 98% yield). MS (ESI) m/z: 486.9 (M+H)+. 1H NMR (400 MHz, chloroform-d) δ ppm 8.00-8.12 (m, 2H) 7.49 (d, J=8.79 Hz, 1H) 7.24-7.45 (m, 5H) 5.11-5.32 (m, 2H) 4.57 (d, J=16.26 Hz, 2H) 4.10-4.33 (m, 4H) 2.89 (d, J=3.95 Hz, 3H) 2.44 (t, J=7.25 Hz, 2H) 1.15-1.34 (m, 6H) 0.81-1.05 (m, 3H).

Workup

  1. stirringAfter 20 min stirring
  2. temperatureThe reaction mixture was heated at 65° C. over night
  3. customThe reaction was quenched with water
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-8c6edff82c1a4ea3a7089a457a396705
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

Loading…