Methyl iodide → HCID 70011850, compound

HRID 1369003Notes

Reaction equation

HRID 1369003 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][CH:10]2[C:13]([O:15][CH3:16])=[O:14])=[CH:5][CH:4]=1.[CH3:17]I.[H-].[Na+]>CN(C=O)C>[CH3:16][O:15][C:13]([C:10]1([CH3:17])[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=2)[CH2:7][CH2:8][CH2:9]1)=[O:14]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 23567164HCID 23567164, compound

Product 1

HCID 70011850HCID 70011850, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-Methoxytetralin-1-yl-carboxylic acid, methyl ester (0.4 g; 1.8 mmol; from step (i) above) and MeI (0.13 mL, 2.0 mmol) were added to a slurry of NaH (55% in oil; 87 mg; 2.0 mmol) in DMF (5 mL) and the mixture was stirred at RT overnight. The resultant mixture was poured onto water, and the water mixture was extracted with EtOAc:toluene 3 times. The combined organic layer was washed with water, dried (Na2SO4), and concentrated. Flash chromatography (Si-gel; heptane:EtOAc; 4:1) yielded 0.18 g (42%) of the sub-title compound.

Workup

  1. extractionthe water mixture was extracted with EtOAc
  2. washThe combined organic layer was washed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c1a23f9162b543d58bbb7ba6210db382
Source dataset
uspto-grants-2003_06
Patent number
US06576657B2

Reaction notes

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