Benzyl Bromide → HCID 69745557, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH:5]([C:11]([C:13]1[NH:14][CH:15]=[CH:16][CH:17]=1)=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>COCCOC.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:18])[C:5]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:11]([C:13]1[NH:14][CH:15]=[CH:16][CH:17]=1)=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]Participants
Procedure
2-(1H-Pyrrole-2-carbonyl)-malonic acid diethyl ester (0.79 mmol, 0.21 g) in DME (3 ml) was treated with lithium bis-trimethylsilylamide (0.79 mmol, 133 mg). The resulting solution was held at room temperature for 30 minutes, then treated with benzyl bromide (0.79 mmol, 0.10 ml). The resulting solution was held at room temperature overnight, then diluted with ethyl acetate (30 ml), and washed with saturated ammonium chloride (10 ml), followed by brine (20 ml). The organics were concentrated under reduced pressure and the residue was purified by silica gel chromatography to provide 0.23 g (84%) of 2-benzyl-2-(1H-pyrrole-2-carbonyl)-malonic acid diethyl ester. 1H NMR (CDCl3) δ10.01 (1H, s), 7.25-7.17 (4H, m), 7.14 (1H, dt, J=2.7, 1.3), 7.03-6.98 (1H, m), 6.86 (1H, ddd, J=3.8, 2.4, 1.3), 6.29-6.25 (1H, m), 4.22 (4H, q, J=7.1), 3.47 (2H, s), 3.39 (2H, s), 1.25 (6H, t, J=1.7).
Workup
- waitThe resulting solution was held at room temperature overnight
- washwashed with saturated ammonium chloride (10 ml)
- concentrationThe organics were concentrated under reduced pressure
- customthe residue was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-0d32645c0a8e4173bc11290e5ec3217d
- Source dataset
- uspto-grants-2003_08
- Patent number
- US06610730B2
Reaction notes
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