Dimethyl malonate → HCID 57543483, compound
Reaction equation
[H-].[Na+].[C:3]([O:10][CH3:11])(=[O:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6].[CH2:12]([C@@H:15]1[CH2:19]OS(=O)(=O)O1)[CH2:13][CH3:14].C([O-])(=O)CC([O-])=O>COCCOC.[Cl-].[Na+].O>[CH3:8][O:7][C:5]([C:4]1([C:3]([O:10][CH3:11])=[O:9])[CH2:14][C@@H:13]1[CH2:12][CH2:15][CH3:19])=[O:6]Participants
Conditions
- Temperature
- 0 °C
Procedure
To a stirred suspension of NaH 60% (873 mg, 21.81 mmol) in dry 1,2-dimethoxyethane (48 mL) is added dropwise dimethyl malonate (1.31 g, 9.92 mmol) at room temperature over 10 minutes under a nitrogen atmosphere. A solution of (VIII) (1.82 g, 10.96 mmol) in dry 1,2-dimethoxyethane (5 mL) is added slowly to the malonate anion solution, and the resulting mixture is refluxed for 2 hours and then cooled to 0° C. After adding brine (30 mL), the mixture is extracted with diethyl ether (50 mL, 25 mL). The combined organic layers are dried over anhydrous MgSO4, and concentrated under reduced pressure. The crude is purified by column chromatography (cyclohexane: EtOAc=90:10) to afford 1.28 g of (IId) (6.40 mmol, 65%, ee=78.2%) as a colorless oil.
Workup
- temperaturethe resulting mixture is refluxed for 2 hours
- extractionthe mixture is extracted with diethyl ether (50 mL, 25 mL)
- dry with materialThe combined organic layers are dried over anhydrous MgSO4
- concentrationconcentrated under reduced pressure
- customThe crude is purified by column chromatography (cyclohexane: EtOAc=90:10)
- customto afford 1.28 g of (IId) (6.40 mmol, 65%, ee=78.2%) as a colorless oil
Sources & evidence
- ORD record
- ord-3babf7d3f0ee46a7bee40d87a21cfe2e
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08076493B2
Reaction notes
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