Hexanoic Acid → ETHYL 7-METHYL-3-OXOOCTANOATE
Reaction equation
C[C:2]1([CH3:10])[O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])O1.C(O)(=O)[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[CH2:19]1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:19][CH:13]([CH3:12])[CH2:14][CH2:15][CH2:16][C:4](=[O:5])[CH2:6][C:7]([O:9][CH2:2][CH3:10])=[O:8]Participants
Procedure
To a stirred solution of Meldrum's Acid (2.0 g, 13.9 mmol) in 100 mL of CH2Cl2, hexanoic acid (1.61 g, 13.9 mmol) was added followed by DMAP (3.39 g, 27.8 mmol) and finally DCC (2.86 g, 13.9 mmol). The reaction stirred overnight at room temperature. The mixture was then filtered and the filtrate washed with 1M HCl, H2O and Brine. The organics were then dried over sodium sulfate, filtered and concentrated to a yellow oil. The material was then dissolved in 100 mL of EtOH and refluxed overnight. The reaction mixture was concentrated to yield 2.58 g (99%) of a clear oil. No purification performed: 1H NMR (CDCl3, 400 MHz) δ 4.22–4.12 (q, 2H, J=7.07), 3.40 (s, 2H), 2.56–2.44 (t, 2H, J=7.42), 1.69–1.43 (m, 3H), 1.30–1.21 (t, 3H, J=7.07), 1.19–1.09 (m, 2H), 0.89–0.81 (d, 6H, J=6.55).
Workup
- filtrationThe mixture was then filtered
- washthe filtrate washed with 1M HCl, H2O and Brine
- dry with materialThe organics were then dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated to a yellow oil
- dissolutionThe material was then dissolved in 100 mL of EtOH
- temperaturerefluxed overnight
- concentrationThe reaction mixture was concentrated
Sources & evidence
- ORD record
- ord-fc0478a1d9ec421b8a7f3c513b4ad7ef
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07189851B2
Reaction notes
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