HCID 131726169, compound → HCID 58764112, compound

HRID 2387067Notes

Reaction equation

HRID 2387067 reaction equation
C([SiH2]O[C:7](C)(C)[C:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]([CH:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)([OH:27])[CH2:17][C:18]2[O:23][C:22]([CH3:25])([CH3:24])[O:21][C:20](=[O:26])[CH:19]=2)=[CH:10][C:9]=1[CH2:33][CH3:34])(C)(C)C>CCO.[OH-].[OH-].[Pd+2]>[CH:28]1([C:16]([OH:27])([CH2:15][CH2:14][C:11]2[CH:12]=[CH:13][C:8]([CH3:7])=[C:9]([CH2:33][CH3:34])[CH:10]=2)[CH2:17][C:18]2[O:23][C:22]([CH3:24])([CH3:25])[O:21][C:20](=[O:26])[CH:19]=2)[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

4

Reactant 1

HCID 131726169HCID 131726169, compound

Product 1

HCID 58764112HCID 58764112, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of 6-{4-[4-(tert-butyl-dimethyl-silanyloxymethyl)-3-ethyl-phenyl]-2-cyclopentyl-2-hydroxy-but-3-ynyl}-2,2-dimethyl-[1,3]dioxin-4-one (1.0 g) in EtOH (50 mL) was added Pd(OH)2 (20 wt %, 100 mg). The reaction was stirred under H2 atmosphere for 15 hours. The reaction was filtered through a pad of celite and the solvent was removed under reduced pressure to afford the desired product. 1H NMR (300 MHz, CDCl3): δ 1.19 (t, J=7.5 Hz, 3 H), 1.43-1.69 (m, 8 H), 1.71 (s, 6 H), 1.79-1.85 (m, 2 H), 2.05-2.16 (m, 1 H), 2.27 (s, 3 H), 2.44-2.66 (m, 6 H), 5.37 (s, 1 H), 6.89-6.95 (m, 2 H), 7.04-7.08 (m, 1 H).

Workup

  1. filtrationThe reaction was filtered through a pad of celite
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-353be32b89c842fe8f525c21c1ab9cb8
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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