Trimethylsilyl triflate → HCID 86633528, compound

HRID 1641585Notes

Reaction equation

HRID 1641585 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[Si]([O:18][S:19]([C:22]([F:25])([F:24])[F:23])(=[O:21])=[O:20])(C)C.C([O-])(O)=O.[Na+]>ClCCl.C(OCC)C>[F:23][C:22]([F:25])([F:24])[S:19]([O:18]/[C:11](=[C:10]1/[CH:2]([CH:1]([CH3:7])[CH3:6])[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:20])=[O:21]

Participants

6

Reactant 3

HCID 65367Trimethylsilyl triflateHCID 516892Sodium BicarbonateHCID 12009091HCID 12009091, compound

Product 1

HCID 86633528HCID 86633528, compoundYield 75%

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 isobudylaldehyde (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 75%).

Workup

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

Sources & evidence

ORD record
ord-d78993a8623848ad83df99e0a2b348f2
Source dataset
uspto-grants-2012_02
Patent number
US08115019B2

Reaction notes

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