2-Naphthalenecarboxaldehyde → HCID 86633524, compound

HRID 1641580Notes

Reaction equation

HRID 1641580 reaction equation
[C:1]1([CH:7](O)[CH2:8][CH2:9][C:10]#[C:11][CH3:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[CH:24]=[O:25].C[Si]([O:30][S:31]([C:34]([F:37])([F:36])[F:35])(=[O:33])=[O:32])(C)C.C([O-])(O)=O.[Na+]>ClCCl.C(OCC)C>[F:35][C:34]([F:37])([F:36])[S:31]([O:33]/[C:11](=[C:10]1/[CH:24]([C:15]2[CH:16]=[CH:17][C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:14]=2)[O:25][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][CH2:9]/1)/[CH3:12])(=[O:32])=[O:30]

Participants

7

Reactant 4

HCID 62012-NaphthalenecarboxaldehydeHCID 65367Trimethylsilyl triflateHCID 516892Sodium BicarbonateHCID 12009091HCID 12009091, compound

Product 1

HCID 86633524HCID 86633524, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

In dichloromethane (3.0 mL) were dissolved 1-phenylhex-4-yn-1-ol (0.28 mmol) and 2-naphthalenealdehyde (0.34 mmol) and the solution was cooled to −78° C. before the addition of trimethylsilyltriflate (TMSOTf) (0.86 mmol) thereto. After being stirred for 1 hour at the same temperature, the reaction solution was slowly heated 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 81%).

Workup

  1. stirringStirring
  2. waitwas further conducted at room temperature for an additional one to two hours in the reaction solution
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe purification of the
  8. concentrationconcentrate through column chromatography

Sources & evidence

ORD record
ord-fe063d0b402d4756a74a724275e95188
Source dataset
uspto-grants-2012_02
Patent number
US08115019B2

Reaction notes

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