Methyl iodide → HCID 66746413, compound

HRID 453929Notes

Reaction equation

HRID 453929 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[O:11][C:7]1([CH2:10][CH2:9][CH2:8]1)[CH2:6][C:5]2=[O:15].[C:16](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O.O>[CH3:16][O:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[O:11][C:7]1([CH2:8][CH2:9][CH2:10]1)[CH2:6][C:5]2=[O:15]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 667463336-Hydroxyspiro[2H-1-benzopyran-2,1′-cyclobutan]-4(3H)-one

Product 1

HCID 66746413HCID 66746413, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To the stirred solution of 6-hydroxyspiro[chromene-2,1′-cyclobutan]-4-(3H)-one (8 g, 39.215 mmol) in dry dimethylformamide (150 ml), potassium carbonate (16.28 g, 117.64 mmol) and methyl iodide (4.88 ml, 78.431 mmol) were added and the reaction mixture was stirred at room temperature under nitrogen atmosphere for 2 h. After the completion of the reaction, the reaction mixture was diluted with water (100 ml), extracted with ethyl acetate (3×300 ml), the combined organic layers washed with water (3×100 ml), brine (60 ml), dried (Na2SO4), filtered and concentrated to yield 8.13 g of the product; 1H NMR (300 MHz, CDCl3) δ 1.67-1.77 (m, 1H), 1.85-1.97 (m, 1H), 2.11-2.18 (m, 2H), 2.23-2.34 (m, 2H), 2.87 (s, 2H), 3.77 (s, 3H), 6.88 (d, J=9.6 Hz, 1H), 7.06 (d, J=8.7 Hz, 1H), 7.25 (s, 1H).

Workup

  1. customAfter the completion of the reaction
  2. extractionextracted with ethyl acetate (3×300 ml)
  3. washthe combined organic layers washed with water (3×100 ml), brine (60 ml)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6335513ff27f4e8fae80d9a231fc799c
Source dataset
uspto-grants-2013_07
Patent number
US08492568B2

Reaction notes

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