HCID 21255986, compound → HCID 59942738, compound

HRID 636895Notes

Reaction equation

HRID 636895 reaction equation
[CH3:1][C:2]1([CH3:30])[CH2:11][CH:10]=[C:9]([C:12]#[C:13][C:14]([CH3:17])([OH:16])[CH3:15])[C:8]2[CH:7]=[C:6](/[CH:18]=[CH:19]/[C:20]3[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=3)[CH:5]=[CH:4][C:3]1=2>N1C=CC=CC=1.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[CH3:1][C:2]1([CH3:30])[CH2:11][CH:10]=[C:9](/[CH:12]=[CH:13]\[C:14]([CH3:15])([OH:16])[CH3:17])[C:8]2[CH:7]=[C:6](/[CH:18]=[CH:19]/[C:20]3[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=3)[CH:5]=[CH:4][C:3]1=2

Participants

4

Reactant 1

HCID 21255986HCID 21255986, compound

Product 1

HCID 59942738HCID 59942738, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 1049PyridineSolvent

Procedure

A mixture of methyl 4-[(E)-(5,6-dihydro-5,5-dimethyl-8-(3-methyl-3-hydroxy-1-butyn-1-yl)-2-naphthalenyl)ethenyl]benzoate (0.228 g, 0.57 mmol) and 10% Pd/BaSO4 (75 mg) in pyridine (5 mL) was hydrogenated (rubber balloon) for 60 minutes at room temperature. The reaction mixture was then filtered through celite and the pad washed with ethyl ether. The filtrate was washed with water, 1N hydrochloric acid and brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified on silica gel chromatography (dichloromethane/acetonitrile) to give the title material (135 mg, 59%) as a white solid.

Workup

  1. customfor 60 minutes
  2. customat room temperature
  3. filtrationThe reaction mixture was then filtered through celite
  4. washthe pad washed with ethyl ether
  5. washThe filtrate was washed with water, 1N hydrochloric acid and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified on silica gel chromatography (dichloromethane/acetonitrile)

Sources & evidence

ORD record
ord-f60b0cbc754049a5bafed0ab338fb315
Source dataset
uspto-grants-2001_02
Patent number
US06194601B1

Reaction notes

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