Methyl iodide → Ethyl 1-methyl-1-(4-methylphenyl)ethanesulfonate

HRID 1274266Notes

Reaction equation

HRID 1274266 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3]C.CC1C=C[C:10]([CH2:13][S:14]([O:17][CH2:18][CH3:19])(=[O:16])=[O:15])=CC=1.I[CH3:21].[CH2:22]1[CH2:26]O[CH2:24][CH2:23]1>>[CH3:21][C:13]([C:22]1[CH:23]=[CH:24][C:2]([CH3:3])=[CH:1][CH:26]=1)([S:14]([O:17][CH2:18][CH3:19])(=[O:15])=[O:16])[CH3:10]

Participants

5

Reactant 4

HCID 6328Methyl iodide2×HCID 8028Tetrahydrofuran2×HCID 12456502Ethyl 4-methylphenylmethanesulfonateHCID 178418339Butyllithium2×

Product 1

HCID 21706484Ethyl 1-methyl-1-(4-methylphenyl)ethanesulfonateYield 77%

Conditions

Temperature
-40 °C

Procedure

To a solution of butyllithium (2.5M in hexanes, 2.94 mL) in THF (3.5 mL) cooled to -60° C. was added ethyl 4-methylphenylmethanesulfonate (1.05 g, 4.91 mmol) in THF (5 mL). After 15 minutes, iodomethane (0.61 mL, 9.8 mmol) was added, and the mixture was stirred for 1 hour at -50 to -30° C. The mixture was recooled to -60° C., and further butyllithium (2.94 mL) and iodomethane (0.61 mL) were added. The reaction was quenched with aqueous ammonium chloride, and extracted with ether. The organic phase was dried (K2CO3), filtered and evaporated. Chromatography of the residue over silica gel (15% ethyl acetate/hexane) gave ethyl 1-methyl-1-(4-methylphenyl)ethanesulfonate (0.917 g, 3.79 mmol, 77%).

Workup

  1. customwas recooled to -60° C.
  2. customThe reaction was quenched with aqueous ammonium chloride
  3. extractionextracted with ether
  4. dry with materialThe organic phase was dried (K2CO3)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-b12cea1cbec74cff9b2f87bce83588e8
Source dataset
uspto-grants-2000_12
Patent number
US06156784

Reaction notes

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