HCID 86727678, compound → HCID 18736515, compound

HRID 1506085Notes

Reaction equation

HRID 1506085 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([Si:15]([C:44]2[CH:49]=[CH:48][C:47]([O:50]CC3C=CC=CC=3)=[CH:46][CH:45]=2)([C:30]2[CH:35]=[CH:34][C:33]([O:36]CC3C=CC=CC=3)=[CH:32][CH:31]=2)[C:16]2[CH:21]=[CH:20][C:19]([O:22]CC3C=CC=CC=3)=[CH:18][CH:17]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>[Pd].C1COCC1>[OH:22][C:19]1[CH:18]=[CH:17][C:16]([Si:15]([C:30]2[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=2)([C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=2)[C:44]2[CH:45]=[CH:46][C:47]([OH:50])=[CH:48][CH:49]=2)=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 86727678HCID 86727678, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18736515HCID 18736515, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A THF (200 mL) solution containing tetrakis(4-benzyloxyphenyl)silane 40 (10.00 g, 13.15 mmol) and 10 wt % palladium on carbon (400 mg) (e.g., catalyst), was placed in the 1000 mL pressure safe vessel equipped with viton seals and, in turn, connected to the hydrogenator, as provided above. The vessel was pressurized with hydrogen (35 psi) and the solution was allowed to react with stirring for 48 hr. The catalyst was removed by filtration through celite, and the solvent was removed under reduced pressure to afford 4.80 g (91% yield) of tetrakis(4-hydroxyphenyl)silane 42 (FIG. 8) as an off-white solid. For purification, tetrakis(4-hydroxyphenyl)silane 42 was dissolved in THF and precipitated out in hexane. The white product was filtered, washed with ether, and dried under dynamic vacuum. NMR assignments of the molecule shown in FIG. 8, include: 1H NMR (acetone-d6) δ: 8.63 (s, 4H), 7.38 (d, J=6 Hz, 8H), 6.81 (d, J=6 Hz, 8H). 13C NMR (acetone-d6) δ: 159.54 (C4), 138.59 (C2), 125.98 (C1), 115.92 (C3). 29Si NMR (acetone-d6) δ: −14.64 (s).

Workup

  1. customas provided above
  2. customto react
  3. customThe catalyst was removed by filtration through celite
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2587b31ce8e841efab1869efdf058a83
Source dataset
uspto-grants-2015_12
Patent number
US09217064B2

Reaction notes

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