HCID 66890954, compound → HCID 66889589, compound

HRID 250176Notes

Reaction equation

HRID 250176 reaction equation
[O:1]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:20]2[CH:25]=[CH:24][C:23]([C:26]#[C:27][CH:28]([OH:33])[C:29]([CH3:32])([CH3:31])[CH3:30])=[C:22]([CH3:34])[CH:21]=2)([CH2:18][CH3:19])[CH2:16][CH3:17])=[CH:11][C:10]=1[CH3:35])[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].[H][H]>[Pd].CO>[O:1]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:20]2[CH:25]=[CH:24][C:23](/[CH:26]=[CH:27]\[CH:28]([OH:33])[C:29]([CH3:32])([CH3:31])[CH3:30])=[C:22]([CH3:34])[CH:21]=2)([CH2:16][CH3:17])[CH2:18][CH3:19])=[CH:11][C:10]=1[CH3:35])[Si:2]([C:5]([CH3:6])([CH3:7])[CH3:8])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 66890954HCID 66890954, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 66889589HCID 66889589, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-(4-{1-[4-(tert-butyl-dimethylsiloxy)-3-methylphenyl]-1-ethylpropyl}-2-methylphenyl)-4,4-dimethylpent-1-yn-3-ol (0.4 g, 0.8 mmol) in anhyd MeOH (10 mL) was sparged with a stream of nitrogen (5 min) and then charged with 5% Pd/C (17 mg). Next an atmosphere of hydrogen (ambient pressure) was introduced into the reaction flask via a hydrogen-filled balloon with an inlet needle. After sparging briefly with hydrogen (5 min), the reaction mixture was stirred 3 h at ambient pressure. The reaction mixture was diluted with EtOAc (30 mL) and filtered through Celite. The filter agent was rinsed with EtOAc, and the combined filtrates were concentrated to yield (Z)-1-(4{-1-[4-(tert-butyl-dimethylsiloxy)-3-methylphenyl]-1-ethylpropyl}-2-methylphenyl)-4,4-dimethylpent-1-en-3-ol (0.28 g, 71%), which was used without purification in the next step.

Workup

  1. additionfilled balloon with an inlet needle
  2. customAfter sparging briefly with hydrogen (5 min)
  3. additionThe reaction mixture was diluted with EtOAc (30 mL)
  4. filtrationfiltered through Celite
  5. washThe filter agent was rinsed with EtOAc
  6. concentrationthe combined filtrates were concentrated

Sources & evidence

ORD record
ord-de67ac7b9dc947f6be240e4ab0571e2e
Source dataset
uspto-grants-2011_01
Patent number
US07863298B2

Reaction notes

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