2-Phenylpropanal → HCID 86633530, compound
Reaction equation
[C:1]1([CH:7]([OH:13])[CH2:8][CH2:9][C:10]#[C:11][CH3:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14]1([CH:20]([CH3:23])C=O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C[Si]([O:28][S:29]([C:32]([F:35])([F:34])[F:33])(=[O:31])=[O:30])(C)C.[C:36]([O-])(O)=O.[Na+]>ClCCl.C(OCC)C>[F:33][C:32]([F:35])([F:34])[S:29]([O:31]/[C:11](=[C:10]1/[CH:36]([CH2:23][CH2:20][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[O:13][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][CH2:9]/1)/[CH3:12])(=[O:30])=[O:28]Participants
Procedure
In dichloromethane (3.0 mL) were dissolved 1-phenylhex-4-yn-1-ol (0.28 mmol) and phenylpropanal (0.34 mmol) and the solution was cooled to −78° C. before the addition of trimethylsilyltriflate (TMSOTf) (0.86 mmol) thereto. At the same temperature, the reaction solution was stirred for 1 hour, followed by slow temperature elevation to room temperature over 3 hours. Stirring was further conducted at room temperature for an additional one to two hours in the reaction solution. After the addition of an aqueous NaHCO3 solution, the reaction solution was diluted with diethylether. The organic layer was washed with water and brine, dried over MgSO4, filtered and concentrated. The purification of the concentrate through column chromatography afforded the title compound (Yield 69%).
Workup
- waitfollowed by slow temperature elevation to room temperature over 3 hours
- stirringStirring
- waitwas further conducted at room temperature for an additional one to two hours in the reaction solution
- washThe organic layer was washed with water and brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe purification of the
- concentrationconcentrate through column chromatography
Sources & evidence
- ORD record
- ord-4a5c65060ff74509baacebfad4c92100
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08115019B2
Reaction notes
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