Methanol → HCID 11171128, compound

HRID 644969Notes

Reaction equation

HRID 644969 reaction equation
[CH3:1][CH:2]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:5](=O)[CH2:4][CH2:3]1.[BH4-].[Na+].[CH3:15]O>>[CH3:1][CH:2]1[C:12]2[C:7](=[CH:8][C:9]([CH3:15])=[CH:10][CH:11]=2)[CH:5]=[CH:4][CH2:3]1

Participants

4

Reactant 3

HCID 887MethanolHCID 892321,2,3,4-Tetrahydro-4-methylnaphthalen-1-oneHCID 4311764Sodium borohydride

Product 1

HCID 11171128HCID 11171128, compoundYield 61%

Procedure

Following a similar procedure to that reported in Ferraz, which is hereby incorporated by reference, to a stirred solution of 4-methyl-α-tetralone (0.867 g, 4.98 mmol) in methanol (20 mL) was added NaBH4 (0.56 g, 14.9 mmol) portionwise. The reaction mixture was followed by TLC and, after complete consumption of the starting material (about 2 h), was quenched with saturated NaHCO3. The aqueous layer was extracted with diethyl ether, dried with magnesium sulfate (MgSO4), and filtered; and the solvent was removed under reduced pressure. The crude alcohol was dissolved in toluene (25 mL) and a few crystals of p-TsOH were added. The reaction mixture was stirred overnight, then neutralized by slow addition of saturated sodium bicarbonate (NaHCO3) and extracted with diethyl ether. The combined organic layers where washed with brine, dried with magnesium sulfate (MgSO4), and filtered; and the solvent was removed under reduced pressure. The product was purified by flash chromatography (SiO2, hexanes) to give 1,2-dihydro-1,6-dimethylnaphthalene ((±)-4) as a clear oil (0.479 g, 61% yield). This compound is volatile and cannot be dried for long periods (>30 min) under high vacuum. The spectroscopic data are consistent with previously reported data (Adachi et al., Bull. Chem. Soc. Jpn., 56:651ff (1983), which is hereby incorporated by reference).

Workup

  1. customafter complete consumption of the starting material (about 2 h)
  2. customwas quenched with saturated NaHCO3
  3. extractionThe aqueous layer was extracted with diethyl ether
  4. dry with materialdried with magnesium sulfate (MgSO4)
  5. filtrationfiltered
  6. customand the solvent was removed under reduced pressure
  7. dissolutionThe crude alcohol was dissolved in toluene (25 mL)
  8. additiona few crystals of p-TsOH were added
  9. additionneutralized by slow addition of saturated sodium bicarbonate (NaHCO3)
  10. extractionextracted with diethyl ether
  11. washThe combined organic layers where washed with brine
  12. dry with materialdried with magnesium sulfate (MgSO4)
  13. filtrationfiltered
  14. customand the solvent was removed under reduced pressure
  15. customThe product was purified by flash chromatography (SiO2, hexanes)

Sources & evidence

ORD record
ord-bae91e29dd3840cfa4359f8bec8c464b
Source dataset
uspto-grants-2010_04
Patent number
US07700798B1

Reaction notes

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