Water → HCID 15464517, compound

HRID 1522725Notes

Reaction equation

HRID 1522725 reaction equation
[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.C[Si]([C:23]#[C:24][C:25]1[CH:26]=[C:27]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=2)[CH:28]=[CH:29][CH:30]=1)(C)C.ClCCl.O>O1CCCC1>[C:24]([C:25]1[CH:26]=[C:27]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=2)[CH:28]=[CH:29][CH:30]=1)#[CH:23]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 2723671Tetrabutylammonium HydroxideHCID 11136557HCID 11136557, compound

Product 1

HCID 15464517HCID 15464517, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetra-n-butylammonium hydroxide (22 cm3, 1 M in methanol) was added to a solution of (16) (1.87 g, 7.4 mmol) in tetrahydrofuran (20 cm3), and the solution was stirred at room temperature for 1 hour. Dichloromethane (20 cm3) and water (50 cm3) were added, and the layers were separated. The aqueous layer was extracted with dichloromethane (3×10 cm3). The combined organic extracts were washed with brine (50 cm3) and dried over magnesium sulfate, and the solvent was removed to leave an orange oil. The crude product was passed through a silica plug using dichloromethane: light petroleum (1:1) as eluent, and the solvent was completely removed to give (17) as a colourless oil (1.31 g, 99%).

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with dichloromethane (3×10 cm3)
  3. washThe combined organic extracts were washed with brine (50 cm3)
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was removed
  6. customto leave an orange oil
  7. customthe solvent was completely removed

Sources & evidence

ORD record
ord-588449d0fe85445893076fba2b9d125a
Source dataset
uspto-grants-2015_07
Patent number
US09078330B2

Reaction notes

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