Ammonium Chloride → HCID 12764994, compound
Reaction equation
[C:1]([Si:5]([CH3:11])([CH3:10])[O:6][CH2:7][C:8]#[CH:9])([CH3:4])([CH3:3])[CH3:2].C([Mg]Cl)(C)C.[Li+].[Cl-].CON(C)[C:22](=[O:24])[CH3:23].[NH4+].[Cl-]>C1COCC1>[Si:5]([O:6][CH2:7][C:8]#[C:9][C:22](=[O:24])[CH3:23])([C:1]([CH3:3])([CH3:4])[CH3:2])([CH3:10])[CH3:11]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
To a −40° C. solution of tert-butyl(dimethyl)(prop-2-yn-1-yloxy)silane (1.70 g, 10 mmol) in THF (6 mL) was added iPrMgCl.LiCl (8.46 mL, 11 mmol) dropwise keeping the internal temperature below −20° C. A solution of the N-methoxy-N-methylacetamide (1.13 g, 11.0 mmol) in THF (4 mL) was cooled to −10° C. and the alkyne solution was added to the Weinreb amide solution via cannula. The reaction mixture was stirred at −10° C. for 10 minutes. The reaction mixture was poured into a mixture of saturated NH4Cl and ice. The aqueous layer was extracted with EtOAc. The organic layer was washed with brine, dried with Mg2SO4, filtered, then concentrated under vacuum to give 5-{[tert-butyl(dimethyl)silyl]oxy}pent-3-yn-2-one (Cpd G, 1.5 g, 64%) as an oil.
Workup
- customthe internal temperature below −20° C
- extractionThe aqueous layer was extracted with EtOAc
- washThe organic layer was washed with brine
- dry with materialdried with Mg2SO4
- filtrationfiltered
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-a0c48b8475a24d03a30a765b372359c5
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09040515B2
Reaction notes
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