Toluene → HCID 131729269, compound

HRID 556131Notes

Reaction equation

HRID 556131 reaction equation
C1(C)C=CC=CC=1.[CH2:8]([CH:11]([CH2:30][CH:31]=[CH2:32])[CH2:12][O:13][SiH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[C:22]C(C)(O)CC(C)C)=[CH:17][CH:16]=1)[CH:9]=[CH2:10].[OH-].[Na+]>C(Cl)Cl>[CH2:30]([CH:11]([CH2:8][CH:9]=[CH2:10])[CH2:12][O:13][SiH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[CH:22])=[CH:17][CH:16]=1)[CH:31]=[CH2:32]

Participants

5

Reactant 3

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 131729268HCID 131729268, compound

Product 1

HCID 131729269HCID 131729269, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

Firstly, dist. toluene (5 mL) was added to and dissolved in 1-(diallylethoxysilyl)-4-(3,5-dimethyl-3-hydroxy-hexynyl)benzene (125 mg, 0.35 mmol) obtained in Synthesis example 10. The resultant mixture was added with NaOH (9.9 mg, 0.25 mmol), and then was stirred under a nitrogen atmosphere at 80° C. for 16 hours to obtain a reaction mixture. Then, the reaction mixture was diluted with CH2Cl2, and an organic layer was washed with dist. H2O and sat. NaCl. The organic layer thus collected was dried with MgSO4, and the dried organic layer was filtered and concentrated to obtain a crude product. The obtained crude product was separated and purified by silica gel column chromatography (hexane/EtOAc=5/1) to obtain 1-(diallylethoxysilyl)-4-ethynylbenzene (5 mg, 6% yield).

Workup

  1. customobtained in Synthesis example 10
  2. customto obtain a reaction mixture
  3. washan organic layer was washed with dist
  4. customThe organic layer thus collected
  5. dry with materialwas dried with MgSO4
  6. filtrationthe dried organic layer was filtered
  7. concentrationconcentrated
  8. customto obtain a crude product
  9. customThe obtained crude product
  10. customwas separated
  11. custompurified by silica gel column chromatography (hexane/EtOAc=5/1)

Sources & evidence

ORD record
ord-b5e00d7f33c646e7a88cc0beb97ee03f
Source dataset
uspto-grants-2011_11
Patent number
US08053588B2

Reaction notes

Loading…