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

HRID 1387266Notes

Reaction equation

HRID 1387266 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-9df3ae5750264a0fb0df3355a01795fc
Source dataset
uspto-grants-2001_07
Patent number
US06268365B1

Reaction notes

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