HCID 67144993, compound → HCID 86677210, compound

HRID 630380Notes

Reaction equation

HRID 630380 reaction equation
[CH3:1][Si:2]([CH3:25])([C:21]([CH3:24])([CH3:23])[CH3:22])[O:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13]CC1C=CC=CC=1>CO.[Pd]>[Si:2]([O:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][OH:13])([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:25])[CH3:1]

Participants

4

Reactant 1

HCID 67144993HCID 67144993, compound2×

Product 1

HCID 86677210HCID 86677210, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 13,13,14,14-tetramethyl-1-phenyl-2,5,12-trioxa-13-silapentadecane (intermediate 15; 3.1 g, 0.008 mol) in methanol (74 mL) was added palladium on charcoal (10%, 0.3 g). The mixture was stirred overnight at room temperature under hydrogen (balloon pressure). The catalyst was filtered and the filtrate was evaporated under reduced pressure giving crude, which was purified by column chromatography with silica gel, eluting with hexane/ethyl acetate (from 9:1 to 4:1) to give the title compound as a colourless oil (77%).

Workup

  1. filtrationThe catalyst was filtered
  2. customthe filtrate was evaporated under reduced pressure
  3. customgiving crude, which
  4. customwas purified by column chromatography with silica gel
  5. washeluting with hexane/ethyl acetate (from 9:1 to 4:1)

Sources & evidence

ORD record
ord-0734187b162d4003ab093f74a61342e4
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

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