4-Nitrobenzaldehyde → HCID 11858516, compound

HRID 132758Notes

Reaction equation

HRID 132758 reaction equation
[C:1]1([CH:7](O)[CH2:8][C:9]#[C:10][CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:13]([C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=1)([O-:15])=[O:14].[F:24][C:25]([F:35])([F:34])[S:26]([O:29][Si](C)(C)C)(=[O:28])=[O:27].C([O-])(O)=O.[Na+]>C(Cl)Cl.C(OCC)C>[F:24][C:25]([F:35])([F:34])[S:26]([O:29]/[C:10](=[C:9]1/[C@H:20]([C:19]2[CH:18]=[CH:17][C:16]([N+:13]([O-:15])=[O:14])=[CH:23][CH:22]=2)[O:21][C@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8]/1)/[CH3:11])(=[O:28])=[O:27]

Participants

7

Reactant 4

HCID 5414-NitrobenzaldehydeHCID 65367Trimethylsilyl triflateHCID 516892Sodium BicarbonateHCID 10374709HCID 10374709, compound

Product 1

HCID 11858516HCID 11858516, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

1-Phenylpent-3-yn-1-ol (50 mg, 0.31 mmol) and 4-nitrobenzaldehyde (0.057 mg, 0.37 mmol) were dissolved in methylene chloride (3.0 mL). After the temperature was lowered to −78° C., trimethylsilyl trifluoromethanesulfonate (TMSOTf) (170 mL, 0.93 mmol) was added, and the solution was stirred for one hour at the same temperature. The temperature was slowly elevated to room temperature for about 3 hours, and the solution was further stirred for another one hour at room temperature. The solution was added with an aqueous NaHCO3 solution and diluted with diethylether. The organic layer was washed with water and brine, dried with MgSO4, filtered and condensed. A pure target compound (31 mg) was obtained with a yield of 77% by using column chromatography.

Workup

  1. customwas lowered to −78° C.
  2. waitThe temperature was slowly elevated to room temperature for about 3 hours
  3. stirringthe solution was further stirred for another one hour at room temperature
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. customcondensed

Sources & evidence

ORD record
ord-91f98797d10247a7a2166c4d329e0826
Source dataset
uspto-grants-2008_06
Patent number
US07388101B1

Reaction notes

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