5-Hydroxy-1-tetralone → HCID 67111959, compound

HRID 2363118Notes

Reaction equation

HRID 2363118 reaction equation
[CH3:1][C:2]([O-:5])(C)[CH3:3].[K+].O[C:8]1[CH:17]=[CH:16]C=[C:14]2[C:9]=1[CH2:10][CH2:11][CH2:12]C2=O>CCOCC>[CH2:14]=[C:9]1[CH2:10][CH2:11][CH2:12][C:3]2[C:2]([OH:5])=[CH:1][CH:16]=[CH:17][C:8]1=2

Participants

4

Reactant 2

HCID 1199215-Hydroxy-1-tetraloneHCID 23665647Potassium tert-butoxide

Product 1

HCID 67111959HCID 67111959, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

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. stirringThe mixture was stirred at room temperature overnight
  2. filtrationfiltered through a celite pad
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe crude residue was purified by short column chromatography
  5. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-96a6812d48d34b6097b6410142c1c08b
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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