Reaction equation
[CH3:1][C:2]([CH3:8])=[CH:3]CCC#C.[CH3:9]N(P(N(C)C)(N(C)C)=O)C.[Cl-].[CH3:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].[CH3:27][CH2:28][O:29]C(C)=O>C1COCC1.CCCCCC.CCOCC>[CH3:9]/[C:23](/[CH2:22][CH2:21][CH:3]=[C:2]([CH3:1])[CH3:8])=[CH:24]\[CH2:25][CH2:26][CH2:27][CH2:28][OH:29]Participants
Procedure
A solution of 198 mL (58.0 mmol) of 0.29M Example 1, Part B-(2) Grignard reagent in THF and 48 mL (275.9 mmol) of HMPA at 0° C. under argon was treated dropwise with 2.0 g (11.6 mmol) of Example 6, Part A chloride in 20 mL of THF. After addition, the reaction was allowed to warm to room temperature for 2 hours, at which point the reaction was diluted with 1:1 hexane/ether and quenched with 1N HCl solution. THe organic layer was washed with 1N HCl followed by water, saturated sodium bicarbonate, brine, dried over MgSO4 and evaporated to provide 3.59 g of crude oil. Flash chromatography was performed on 360 g of silica gel packed and loaded with 10:1 hexane/EtOAc and eluted with 7:1 hexane/ EtOAc collecting 30 mL fractions. Fractions 32 to 49 were combined and evaporated to provide 1.68 g (74%) of title compound in the form of an oil.
Workup
- customat 0° C.
- additionAfter addition
- customquenched with 1N HCl solution
- washTHe organic layer was washed with 1N HCl
- dry with materialdried over MgSO4
- customevaporated
- customto provide 3.59 g of crude oil
- washeluted with 7:1 hexane/ EtOAc collecting 30 mL fractions
- customevaporated
Sources & evidence
- ORD record
- ord-b9e6498772594cfd863c233c393a8d7d
- Source dataset
- uspto-grants-1995_06
- Patent number
- US05428028
Linked notes
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