HCID 23498911, compound → HCID 23498920, compound

HRID 1836881Notes

Reaction equation

HRID 1836881 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C:7]#[C:8][C:9]1[C:10]([CH:23]=[O:24])=[CH:11][C:12]2[C:13]([CH3:22])([CH3:21])[CH2:14][CH2:15][C:16]([CH3:20])([CH3:19])[C:17]=2[CH:18]=1.[H][H]>C(O)C.[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[CH2:7][CH2:8][C:9]1[C:10]([CH:23]=[O:24])=[CH:11][C:12]2[C:13]([CH3:22])([CH3:21])[CH2:14][CH2:15][C:16]([CH3:19])([CH3:20])[C:17]=2[CH:18]=1

Participants

5

Reactant 2

HCID 23498911HCID 23498911, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23498920HCID 23498920, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 0.362 g (1.14 mmol) of 3-(2-(2-pyrimidyl)ethynyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthaldehyde in 20 mL of ethanol was added 0.060 g of 10% palladium on carbon and the suspension was shaken under 40 psi hydrogen gas for 3 hours. The resulting solution was filtered and concentrated in vacuo. The product was purified by flash chromatography on silica gel (30% ethyl acetate/hexane) to afford 0.251 g (68%) of 3-(2-(2-pyrimidyl)ethyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthaldehyde (m.p.=78.0-84.5° C.).

Workup

  1. filtrationThe resulting solution was filtered
  2. concentrationconcentrated in vacuo
  3. customThe product was purified by flash chromatography on silica gel (30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-bf7c9863d22142d4b0f3cc1b18d360ac
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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