HCID 67111959, compound → HCID 21842064, compound

HRID 2363119Notes

Reaction equation

HRID 2363119 reaction equation
[CH2:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[C:7]([OH:12])=[CH:6][CH:5]=[CH:4][C:3]1=2.[H][H]>CO.CCOC(C)=O.[Pd]>[CH3:1][CH:2]1[CH2:11][CH2:10][CH2:9][C:8]2[C:7]([OH:12])=[CH:6][CH:5]=[CH:4][C:3]1=2

Participants

6

Reactant 2

HCID 67111959HCID 67111959, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21842064HCID 21842064, compoundYield 36%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of CH3PPh3I (897 mg, 2.22 mmol) in Et2O (10 mL) was added t-BuOK (249 mg, 2.22 mmol). The mixture was stirred for 15 minutes, to which was added dropwise 5-hydroxy-3,4-dihydro-2H-naphthalen-1-one (300 mg, 1.85 mmol). The mixture was stirred at room temperature overnight, diluted with diethylether, and then filtered through a celite pad. The filtrate was concentrated under reduced pressure. The crude residue was purified by short column chromatography and was concentrated under reduced pressure to give 5-methylene-5,6,7,8-tetrahydro-naphthalen-1-ol. A mixture of 5-methylene-5,6,7,8-tetrahydro-naphthalen-1-ol and 10% Pd/C (40 mg) in methanol (10 ml) was hydrogenated under 50 psi hydrogen atmosphere for 1 hour. The mixture was dissolved in EtOAc, filtered through a celite pad. The filtrate was concentrated under reduced pressure, and dried to give 5-methyl-5,6,7,8-tetrahydro-naphthalen-1-ol (110 mg, 36%).

Workup

  1. filtrationfiltered through a celite pad
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customdried

Sources & evidence

ORD record
ord-b025fe655150477f9f70bf8fe1a9c49f
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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