Methyl iodide → Methyl 4-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)benzoate

HRID 1443419Notes

Reaction equation

HRID 1443419 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8]([C:11]3[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=3)=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.IC.[C:22](=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[O:1]1[C:5]2([CH2:10][CH2:9][C:8]([C:11]3[CH:12]=[CH:13][C:14]([C:15]([O:17][CH3:22])=[O:16])=[CH:18][CH:19]=3)=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 595560954-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)benzoic acid

Product 1

HCID 22730331Methyl 4-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)benzoateYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)benzoic acid (572 mg, 2.20 mmol), iodomethane (140 μL, 2.24 mmol), and cesium carbonate (710 mg, 2.17 mmol) in 6 mL of DMF was stirred at rt for 16 h. The mixture was diluted with H2O (10 mL) and extracted with Et2O (100 mL). The organic layer was separated, dried over MgSO4, and concentrated. Chromatography on a Biotage 40S cartridge using 3:17 v/v EtOAc/hexanes as the eluant afforded 399 mg (72%) of the title compound.

Workup

  1. extractionextracted with Et2O (100 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-dbc79623aa6c48939795b3758fb1fa55
Source dataset
uspto-grants-2010_02
Patent number
US07659294B2

Reaction notes

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