Methyl iodide → HCID 86749651, compound

HRID 1735800Notes

Reaction equation

HRID 1735800 reaction equation
[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[C:10]2[C:6]([C:7](=[O:13])[O:8][CH2:9]2)=[C:5]([NH:14][C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])[C:4]=1[CH2:21]/[CH:22]=[C:23](\[CH3:30])/[CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27].[C:31](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O>[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[C:10]2[C:6]([C:7](=[O:13])[O:8][CH2:9]2)=[C:5]([N:14]([C:15](=[O:20])[C:16]([F:17])([F:18])[F:19])[CH3:31])[C:4]=1[CH2:21]/[CH:22]=[C:23](\[CH3:30])/[CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86748887HCID 86748887, compound

Product 1

HCID 86749651HCID 86749651, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.35 g (0.82 mmol) of methyl (E)-6-[1,3-dihydro-6-methoxy-7-methyl-4-(trifluoroacetylamino)-3-oxoisobenzofuran-5-yl]-4-methyl-4-hexenoate in 4 ml of dimethylformamide was added 0.47 g (3.40 mmol) of potassium carbonate and 0.23 ml (3.69 mmol) of iodomethane. The mixture was stirred for 24 hours and then partitioned between ethyl acetate and water. The organic layer was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure to give methyl (E)-6-[1,3-dihydro-6-methoxy-7-methyl-4-(N-trifluoroacetyl-N-methylamino)-3-oxoisobenzofuran-5-yl]-4-methyl-4-hexenoate, an oil. NMR: δ 5.22-5.17 (multiplet ("m"), 2H); 5.10-5.04 (broad triplet, 1H); 3.81 (singlet ("s"), 3H); 3.62 (s, 3H); 3.42-3.27 (m, 5H); 2.45-2.25 (m, 5H); 1.75 (s, 3H).

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7ef15306ddf946b69f520dc8af8e4632
Source dataset
uspto-grants-1996_07
Patent number
US05538969

Reaction notes

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