HCID 22855814, compound → HCID 22855816, compound

HRID 1757697Notes

Reaction equation

HRID 1757697 reaction equation
[C:1]([O:7][CH2:8][C@H:9]([CH3:38])[CH2:10][C@H:11]([O:36][CH3:37])[C@@H:12]([O:28]CC1C=CC=CC=1)[C@@H:13]([O:26][CH3:27])[CH2:14][C@@H:15]([CH3:25])[CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]>[OH-].[OH-].[Pd+2]>[C:1]([O:7][CH2:8][C@H:9]([CH3:38])[CH2:10][C@H:11]([O:36][CH3:37])[C@@H:12]([OH:28])[C@@H:13]([O:26][CH3:27])[CH2:14][C@@H:15]([CH3:25])[CH2:16][O:17][Si:18]([C:21]([CH3:22])([CH3:23])[CH3:24])([CH3:19])[CH3:20])(=[O:6])[C:2]([CH3:5])([CH3:3])[CH3:4]

Participants

3

Reactant 1

HCID 22855814HCID 22855814, compound

Product 1

HCID 22855816HCID 22855816, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

Procedure

Benzyl ether 23 (3.58 g, 6.48 mmol) was dissolved in 50 ml of ethyl acetateand treated with 950 mg of 20% palladium hydroxide on carbon. Hydrogen gas was bubbled into the solution at 25° C. for 1 hr. The mixture was filtered through celite and concentrated in vacuo to give 2.98 g of the alcohol 24 as an oil. This material was used directly in the subsequent transformation.

Workup

  1. customHydrogen gas was bubbled into the solution at 25° C. for 1 hr
  2. filtrationThe mixture was filtered through celite and
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-01983d198ba04b56b790332fafe632b8
Source dataset
uspto-grants-1995_08
Patent number
US05446158

Reaction notes

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