HCID 86727678, compound → HCID 18736515, compound

HRID 1773854Notes

Reaction equation

HRID 1773854 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-2d430932bbd34bd1ad3a4aa65e60f4c8
Source dataset
uspto-grants-2016_02
Patent number
US09255186B2

Reaction notes

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