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

HRID 1880802Notes

Reaction equation

HRID 1880802 reaction equation
[Na].[O-][CH2:3]CCC.COC1C=[C:17]2[C:12]([CH2:13][CH2:14][C:15](=[O:19])[CH2:16]2)=[CH:11][CH:10]=1.CI.[CH2:22]1[CH2:26][O:25][CH2:24][CH2:23]1>CCOC(C)=O.O>[CH3:24][O:25][C:26]1[CH:22]=[C:23]2[C:12]([CH2:17][CH2:16][C:15](=[O:19])[C:14]2([CH3:13])[CH3:3])=[CH:11][CH:10]=1

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 8028Tetrahydrofuran2×HCID 777857-Methoxy-2-tetraloneHCID 5360545SodiumHCID 12476378Butan-1-olate

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A slurry of sodium tent 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-df7b8ea4768044e2ab46a4aed5572ae3
Source dataset
uspto-grants-2012_11
Patent number
US08318765B2

Reaction notes

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