Water → 7-Methoxy-1,1-dimethyl-3,4-dihydronaphthalen-2(1H)-one

HRID 1846597Notes

Reaction equation

HRID 1846597 reaction equation
[CH3:1]C(C)([O-])C.[Na+].COC1C=[C:17]2[C:12]([CH2:13][CH2:14][C:15](=[O:19])[CH2:16]2)=[CH:11][CH:10]=1.CI.O.[CH2:23]1[CH2:27][O:26][CH2:25][CH2:24]1>CCOC(C)=O>[CH3:25][O:26][C:27]1[CH:23]=[C:24]2[C:12]([CH2:17][CH2:16][C:15](=[O:19])[C:14]2([CH3:13])[CH3:1])=[CH:11][CH:10]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6328Methyl iodideHCID 8028Tetrahydrofuran2×HCID 777857-Methoxy-2-tetraloneHCID 23676156Sodium t-butoxide

Product 1

HCID 130110077-Methoxy-1,1-dimethyl-3,4-dihydronaphthalen-2(1H)-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A slurry of sodium tert-butoxide (21.1 g, 220 mmol) in THF (100 mL) was cooled to 0° C. A solution of 7-methoxy-3,4-dihydro-1H-napthalen-2-one (17.6 g, 100 mmol) and methyl iodide (30.1 g, 220 mmol) in THF (100 mL) was added dropwise over 40 min, and the reaction mixture was warmed to room temperature after 10 min. Water (200 mL) and EtOAc (600 mL) was added. The layers were separated, the organic layer was washed with water (5×100 mL) and saturated NaCl (100 mL), filtered and dried with Na2SO4 to provide the title compound (20 g).

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with water (5×100 mL) and saturated NaCl (100 mL)
  3. filtrationfiltered
  4. dry with materialdried with Na2SO4

Sources & evidence

ORD record
ord-2d368b1d00384f4a9984b4a3e029ad2d
Source dataset
uspto-grants-2015_02
Patent number
US08952031B2

Reaction notes

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