HCID 68460107, compound → HCID 68458169, compound

HRID 502616Notes

Reaction equation

HRID 502616 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:14](=[O:16])[CH3:15])=[CH:5][C:6]2[CH2:7][CH2:8][CH2:9][CH:10]([CH3:13])[C:11]=2[CH:12]=1.[CH3:17][Mg]Br>C1COCC1>[CH3:1][O:2][C:3]1[C:4]([C:14]([OH:16])([CH3:17])[CH3:15])=[CH:5][C:6]2[CH2:7][CH2:8][CH2:9][CH:10]([CH3:13])[C:11]=2[CH:12]=1

Participants

4

Reactant 2

HCID 68460107HCID 68460107, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 68458169HCID 68458169, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1-(3-Methoxy-5-methyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone (5.1 g, 23.37 mmol) was dissolved in 50 mL dry THF under nitrogen atmosphere, and the resulting solution was cooled in an ice bath. Methyl magnesium bromide (11.69 mL, 35.1 mmol in diethyl ether) was added dropwise, and the solution was stirred for one hour at 0° C., then for four hours at room temperature. The reaction mixture was poured into ice water and extracted with dichloromethane. The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure to provide 5.38 g of 2-(3-methoxy-5-methyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-propan-2-ol as an oil.

Workup

  1. temperaturethe resulting solution was cooled in an ice bath
  2. waitfor four hours at room temperature
  3. extractionextracted with dichloromethane
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-39b981b3c4d845e690ad97d7494a8bf3
Source dataset
uspto-grants-2010_08
Patent number
US07776872B2

Reaction notes

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