Toluene → 8-Methoxy-1,1-dimethyl-3,4-dihydronaphthalen-2(1h)-one
Reaction equation
C[C:2](C)([O-:4])C.[Na+].C[O:8][C:9]1[CH:10]=CC=[C:13]2[C:18]=1[CH2:17]C(=O)CC2.CI.[C:22]1([CH3:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[CH3:2][O:4][C:26]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:27]=1[C:18]([CH3:13])([CH3:17])[C:9](=[O:8])[CH2:10][CH2:28]2Participants
Conditions
- Temperature
- 15 °C
Procedure
To the toluene suspension of sodium t-butoxide (700 mg, 2.5 eq.), 8-methoxy-3,4-dihydro-1H-naphthalen-2-one (Compound W1, 500 mg, 2.9 mmol) was added dropwise at 0° C. After 15 minutes, the solution turned into blackish green color. The mixture solution was added dropwise with methyl iodide (1.03 g, 2.5 eq.) and stirred at 15° C. overnight. Brown solid precipitated. The reaction solution was added to saturated aqueous solution of ammonium chloride/diethyl ether under stirring and cooling. After that, the solution was extracted with diethyl ether, and dried over sodium sulfate. After removing the solvent under reduced pressure, the resulting residues were purified by silica gel column chromatography (ethyl acetate/hexane) to obtain 8-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one (350 mg).
Workup
- additionwas added dropwise at 0° C
- customBrown solid precipitated
- additionThe reaction solution was added to saturated aqueous solution of ammonium chloride/diethyl ether
- stirringunder stirring
- temperaturecooling
- extractionAfter that, the solution was extracted with diethyl ether
- dry with materialdried over sodium sulfate
- customAfter removing the solvent under reduced pressure
- customthe resulting residues were purified by silica gel column chromatography (ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-5330bd5db0564582a08ee64d52b65d0a
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09440922B2
Reaction notes
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