Reaction equation
[C:1]([O:8][CH2:9][CH3:10])(=[O:7])[C:2]([O:4]CC)=O.[O-]CC.[Na+].[C:15]([Si:19]([CH3:28])([CH3:27])[O:20][CH2:21][CH2:22][CH2:23][C:24](=[O:26])[CH3:25])([CH3:18])([CH3:17])[CH3:16]>>[CH2:9]([O:8][C:1](=[O:7])[C:2](=[O:4])[CH2:25][C:24](=[O:26])[CH2:23][CH2:22][CH2:21][O:20][Si:19]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:27])[CH3:28])[CH3:10]Participants
4
Conditions
- Temperature
- 0 °C
Procedure
Diethyl oxalate (4.048 g, 37.7 mmol) was added to solid sodium ethoxide (0.472 g, 69.3 mmol) at 0° C. followed by slow addition of 5-(tert-butyl-dimethyl-silanyloxy)-pentan-2-one (1.500 g, 69.3 mmol). The resulting orange solution was stirred at 0° C. for 10 minutes and at room temperature for 3 h. Purification by flash chromatography (19:1 hexanes:EtOAc to 9:1 EtOAc:MeOH) provided the title compound (1.982 g); MS 317 (M+1).
Workup
- customPurification by flash chromatography (19:1 hexanes:EtOAc to 9:1 EtOAc:MeOH)
Sources & evidence
- ORD record
- ord-27e5f57cbf0242b7b46f3a85fed10a0b
- Source dataset
- uspto-grants-2001_09
- Patent number
- US06288120B1
Linked notes
Loading…