Water → 871012-92-9

HRID 1522714Notes

Reaction equation

HRID 1522714 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:9][CH:8]=1)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl.O>O1CCCC1>[C:6]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:9][CH:8]=1)#[CH:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 2724141Tetrabutylammonium FluorideHCID 692372572-[4-[2-(Trimethylsilyl)ethynyl]phenyl]pyridine

Product 1

HCID 86084841871012-92-9Yield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (2) (2.26 g, 8.97 mmol) and tetrabutylammonium fluoride (1 M in tetrahydrofuran, 36 mL, 36 mmol) in tetrahydrofuran was stirred at room temperature under argon for 3 hours. Dichloromethane (100 mL) and water (150 mL) were added. The organic layer was separated and the aqueous layer was extracted with dichloromethane (3×15 mL). The combined organic layers were washed with brine (200 mL), dried over anhydrous magnesium sulfate, filtered and the solvent completely removed. The residue was purified by passing through a silica plug using dichloromethane as eluent to give (3) (1.44 g, 90%).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with dichloromethane (3×15 mL)
  3. washThe combined organic layers were washed with brine (200 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent completely removed
  7. customThe residue was purified

Sources & evidence

ORD record
ord-36fe1fb911cf4719bd5f1ea438ae9d0d
Source dataset
uspto-grants-2015_07
Patent number
US09078330B2

Reaction notes

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