HCID 131730735, compound → HCID 131730738, compound

HRID 455998Notes

Reaction equation

HRID 455998 reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:27])([CH3:26])[C:8]12[O:15][C:12]([C:16]([CH3:24])([CH3:23])[O:17][SiH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])([CH:13]=[CH:14]1)[CH2:11][C:10](=[O:25])[CH2:9]2)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([SiH2:5][O:6][C:7]([CH3:27])([CH3:26])[C:8]12[O:15][C:12]([C:16]([CH3:24])([CH3:23])[O:17][SiH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])([CH2:13][CH2:14]1)[CH2:11][C:10](=[O:25])[CH2:9]2)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 131730735HCID 131730735, compound

Product 1

HCID 131730738HCID 131730738, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-8-oxa-bicyclo[3.2.1]-oct-6-en-3-one (200 mg, 4.84 mmol)(Lee, K. and Cha, J. K., J. Amer. Chem. Soc., 123:5590-5591 (2001)) and 5% Pd/C (30 mg) in 10 mL of MeOH was stirred at RT under H2 (balloon pressure) for 8 h. The Pd catalyst was removed by filtration on Celite, and the filtrate was concentrated to give 200 mg (100%) of the title compound as a colorless oil. Mass spectrum (ESI, m/z): Calcd. for C21H42O4Si2, 415.2 (M+H), found 415.1.

Workup

  1. customThe Pd catalyst was removed by filtration on Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-cc23247bf788403d8f9a528c6c3f23af
Source dataset
uspto-grants-2013_07
Patent number
US08497376B2

Reaction notes

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