Carbon Dioxide → HCID 59829865, compound
Reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:7]([Li])[CH2:8][CH2:9][CH3:10].[C:12](=[O:14])=[O:13].S([O-])(O)(=O)=O.[K+].[O:21]1[CH2:25][CH2:24][CH2:23]C1>>[CH2:25]([O:21][C:3]1[CH:2]=[C:1]([O:21][CH2:25][CH:24]=[CH2:23])[C:6]([CH2:7][C:8]#[C:9][CH3:10])=[CH:5][C:4]=1[C:12]([OH:14])=[O:13])[CH:24]=[CH2:23]Participants
Conditions
- Temperature
- -78 °C
Procedure
Crude IM06-c (0.51 g) dissolved in anhydrous tetrahydrofuran (6 mL) was placed in a 50 mL two-neck flask under a nitrogen atmosphere, and after cooling to −78° C., a hexane solution of 1.59M n-butyllithium (1.1 mL, 1.76 mmol) was added dropwise. The reaction mixture was stirred for 1 hour, mixed with dry ice (7 g) and further stirred for 1 hour. The reaction mixture was adjusted to pH 2.5 by mixing with 10% potassium hydrogensulfate and extracted twice with ethyl acetate (40 mL). The organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate. After filtration and evaporation, the residue was purified by silica gel column chromatography (hexane-ethylacetate=2:1) to obtain the title compound (IM07-c:0.28 g, yield 62%, 3 steps).
Workup
- customwas placed in a 50 mL two-neck flask under a nitrogen atmosphere
- stirringfurther stirred for 1 hour
- extractionextracted twice with ethyl acetate (40 mL)
- washThe organic layer was washed with saturated sodium chloride solution
- dry with materialdried over anhydrous sodium sulfate
- filtrationAfter filtration and evaporation
- customthe residue was purified by silica gel column chromatography (hexane-ethylacetate=2:1)
Sources & evidence
- ORD record
- ord-61b8df46fb8243e7aa1e4146303f601d
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399464B2
Reaction notes
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